Heterocyclic compounds as 5ht2a biased agonists

A 5HT2A agonist, comprising a compound having the structure of FORMULA 1,

• wherein,
• A is selected from N, CH or CR6;
• B is selected from N, CH or CR5;
• C is selected from N, CH or CR4;
• D is selected from N or C;
• X is selected from N, CH or CR7;
• Y is selected from N or C;
• R1 and R2 at each occurrence, are independently selected from null, hydrogen, halogen, C1-C8 alkyl, oxo, Ph, C(O)R21, C(O)OR21, C(O)NR21R22, S(O)R21, S(O)2R21, S(O)2NR21R22, optionally substituted C1-C8 alkyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted C1-C8 alkoxy, optionally substituted C1-C8alkoxyC1-C8 alkyl, optionally substituted C1-C8 alkylaminoC1-C8 alkyl, optionally substituted 3-8 membered cycloalkyl, optionally substituted C3-C8 cycloalkoxy, optionally substituted 3-8 membered heterocyclyl, optionally substituted aryl, and optionally substituted heteroaryl;
• wherein
• R21 and R22 are independently selected from hydrogen, optionally substituted C1-C8 alkyl, optionally substituted C1-C8alkoxyC1-C8alkyl, optionally substituted C1-C8alkylaminoC1-C8alkyl, optionally substituted C3-C10 cycloalkyl, optionally substituted 3-20 membered heterocyclyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted aryl, and optionally substituted heteroaryl, or
• R21 and R22, together with the atom to which they are connected form an optionally substituted 3-8 membered cycloalkyl or heterocyclyl ring;
• R4, R5, R6 and R7 at each occurrence, are independently selected from hydrogen, halogen, C1-C8 alkyl, oxo, Ph, CN, NO2, OR2, SR23, NR23R24, C(O)R23, C(O)OR23, C(O)NR23R24, S(O)R23, S(O)2R23, S(O)2NR23R24, NR25C(O)OR23, NR25C(O)R23, NR25C(O)NR23R24, NR25S(O)R23, NR25S(O)2R23, NR25S(O)2NR23R24, optionally substituted C1-C8 alkyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted C1-C8 alkoxy, optionally substituted C1-C8alkoxyC1-C8 alkyl, optionally substituted C1-C8 alkylaminoC1-C8 alkyl, optionally substituted 3-8 membered cycloalkyl, optionally substituted C3-C8 cycloalkoxy, optionally substituted 3-8 membered heterocyclyl, optionally substituted aryl, and optionally substituted heteroaryl;
• wherein
• R23, R24, and R25 are independently selected from hydrogen, optionally substituted C1-C8 alkyl, optionally substituted C1-C8alkoxyC1-C8alkyl, optionally substituted C1-C8alkylaminoC1-C8alkyl, optionally substituted C3-C10 cycloalkyl, optionally substituted 3-20 membered heterocyclyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted aryl, and optionally substituted heteroaryl, or
• R23 and R24, R23 and R25, R24 and R25 together with the atom to which they are connected form an optionally substituted 3-8 membered cycloalkyl or heterocyclyl ring;
• and
• {circle around (z)} at each occurrence is selected from the following groups, or their optionally substituted analogs, wherein * denotes the point of attachment:
• wherein,
• R3 at each occurrence, are independently selected from hydrogen, methyl, ethyl, n-propyl, C1-C8 alkyl, CD3, Ph, C(O)R26, C(O)OR26, C(O)NR26R27, S(O)R26, S(O)2R26, S(O)2NR26R27, optionally substituted C1-C8 alkyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted C1-C8 alkoxy, optionally substituted C1-C8alkoxyC1-C8 alkyl, optionally substituted C1-C8 alkylaminoC1-C8 alkyl, optionally substituted 3-8 membered cycloalkyl, optionally substituted C3-C8 cycloalkoxy, optionally substituted 3-8 membered heterocyclyl, optionally substituted aryl, and optionally substituted heteroaryl;
• wherein
• R26 and R27 are independently selected from hydrogen, optionally substituted C1-C8 alkyl, optionally substituted C1-C8alkoxyC1-C8alkyl, optionally substituted C1-C8alkylaminoC1-C8alkyl, optionally substituted C3-C10 cycloalkyl, optionally substituted 3-20 membered heterocyclyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted aryl, and optionally substituted heteroaryl, or
• R26 and R27, together with the atom to which they are connected form an optionally substituted 3-8 membered cycloalkyl or heterocyclyl ring;
• R17 and R18 at each occurrence, are independently selected from hydrogen, halogen, C1-C8 alkyl, oxo, Ph, CN, NO2, OR28, SR28, NR28R29, C(O)R28, C(O)OR29, C(O)NR28R29, S(O)R28, S(O)2R28, S(O)2NR28R29, NR30C(O)OR28, NR30C(O)R28, NR30C(O)NR28R29, NR30S(O)R28, NR31S(O)2R28, NR30S(O)2NR28R29, optionally substituted C1-C8 alkyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted C1-C8 alkoxy, optionally substituted C1-C8alkoxyC1-C8 alkyl, optionally substituted C1-C8 alkylaminoC1-C8 alkyl, optionally substituted 3-8 membered cycloalkyl, optionally substituted C3-C8 cycloalkoxy, optionally substituted 3-8 membered heterocyclyl, optionally substituted aryl, and optionally substituted heteroaryl;
• wherein;
• R28, R29, and R30 are independently selected from hydrogen, optionally substituted C1-C8 alkyl, optionally substituted C1-C8alkoxyC1-C8alkyl, optionally substituted C1-C8alkylaminoC1-C8alkyl, optionally substituted C3-C10 cycloalkyl, optionally substituted 3-20 membered heterocyclyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted aryl, and optionally substituted heteroaryl, or
• R28 and R29, R28 and R30, R29 and R30 together with the atom to which they are connected form an optionally substituted 3-20 membered cycloalkyl or heterocyclyl ring;
• and
• pharmaceutically acceptable salts thereof.

A 5HT2A agonist, comprising a compound having the structure of FORMULA 2,

• wherein
• A is selected from N, CH or CR6;
• B is selected from N, CH or CR5;
• C is selected from N, CH or CR4;
• D is selected from N or C;
• X is selected from N, CH or CR7;
• Y is selected from N or C;
• n is selected from 0, 1 or 2;
• R1 and R2 at each occurrence, are independently selected from null, hydrogen, halogen, C1-C8 alkyl, oxo, Ph, C(O)R21, C(O)OR21, C(O)NR21R22, S(O)R21, S(O)2R21, S(O)2NR21R22, optionally substituted C1-C8 alkyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted C1-C8 alkoxy, optionally substituted C1-C8alkoxyC1-C8 alkyl, optionally substituted C1-C8 alkylaminoC1-C8 alkyl, optionally substituted 3-8 membered cycloalkyl, optionally substituted C3-C8 cycloalkoxy, optionally substituted 3-8 membered heterocyclyl, optionally substituted aryl, and optionally substituted heteroaryl;
• wherein
• R21 and R22 are independently selected from hydrogen, optionally substituted C1-C8 alkyl, optionally substituted C1-C8alkoxyC1-C8alkyl, optionally substituted C1-C8alkylaminoC1-C8alkyl, optionally substituted C3-C10 cycloalkyl, optionally substituted 3-20 membered heterocyclyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted aryl, and optionally substituted heteroaryl, or
• R21 and R22, together with the atom to which they are connected form an optionally substituted 3-8 membered cycloalkyl or heterocyclyl ring;
• R4, R5, R6 and R7 at each occurrence, are independently selected from hydrogen, halogen, C1-C8 alkyl, oxo, Ph, CN, NO2, OR23, SR23, NR23R24, C(O)R23, C(O)OR23, C(O)NR23R24, S(O)R23, S(O)2R13, S(O)2NR23R24, NR25C(O)OR23, NR25C(O)R23, NR25C(O)NR23R24, NR25S(O)R23, NR25S(O)2R23, NR25S(O)2NR23R24, optionally substituted C1-C8 alkyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted C1-C8 alkoxy, optionally substituted C1-C8alkoxyC1-C8 alkyl, optionally substituted C1-C8 alkylaminoC1-C8 alkyl, optionally substituted 3-8 membered cycloalkyl, optionally substituted C3-C8 cycloalkoxy, optionally substituted 3-8 membered heterocyclyl, optionally substituted aryl, and optionally substituted heteroaryl;
• wherein
• R23, R24, and R25 are independently selected from hydrogen, optionally substituted C1-C8 alkyl, optionally substituted C1-C8alkoxyC1-C8alkyl, optionally substituted C1-C8alkylaminoC1-C8alkyl, optionally substituted C3-C10 cycloalkyl, optionally substituted 3-20 membered heterocyclyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted aryl, and optionally substituted heteroaryl, or
• R23 and R24, R23 and R25, R24 and R25 together with the atom to which they are connected form an optionally substituted 3-8 membered cycloalkyl or heterocyclyl ring;
• R8, R9, R10, R11, R12, R13 and R14, at each occurrence, are independently selected from hydrogen, halogen, C1-C8 alkyl, oxo, Ph, CN, NO2, OR31, SR31, NR31R32, C(O)R31, C(O)OR31, C(O)NR31R32, S(O)R31, S(O)2R31, S(O)2NR31R32, NR33C(O)OR3, NR33C(O)R31, NR33C(O)NR31R32, NR33S(O)R31, NR33S(O)2R31, NR33S(O)2NR31R32, optionally substituted C1-C8 alkyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted C1-C8 alkoxy, optionally substituted C1-C8alkoxyC1-C8alkyl, optionally substituted C1-C8alkylaminoC1-C8 alkyl, optionally substituted 3-8 membered cycloalkyl, optionally substituted C3-C8 cycloalkoxy, optionally substituted 3-8 membered heterocyclyl, optionally substituted aryl, and optionally substituted heteroaryl;
• wherein
• R31, R32, and R33 are independently selected from hydrogen, optionally substituted C1-C8 alkyl, optionally substituted C1-C8alkoxyC1-C8alkyl, optionally substituted C1-C8alkylaminoC1-C8alkyl, optionally substituted C3-C10 cycloalkyl, optionally substituted 3-20 membered heterocyclyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted aryl, and optionally substituted heteroaryl, or
• R31 and R32, R31 and R33, R32 and R33 together with the atom to which they are connected form an optionally substituted 3-8 membered cycloalkyl or heterocyclyl ring;
• R3 is selected from hydrogen, methyl, ethyl, n-propyl, C1-C8alkyl, CD3, Ph, C(O)R26, C(O)OR26, C(O)NR26R27, S(O)R26, S(O)2R26, S(O)2NR26R27, optionally substituted C1-C8 alkyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted C1-C8 alkoxy, optionally substituted C1-C8alkoxyC1-C8alkyl, optionally substituted C1-C8alkylaminoC1-C8 alkyl, optionally substituted 3-8 membered cycloalkyl, optionally substituted C3-C8 cycloalkoxy, optionally substituted 3-8 membered heterocyclyl, optionally substituted aryl, and optionally substituted heteroaryl;
• wherein
• R26 and R27 are independently selected from hydrogen, optionally substituted C1-C8alkyl, optionally substituted C1-C8alkoxyC1-C8alkyl, optionally substituted C1-C8alkylaminoC1-C8alkyl, optionally substituted C3-C10 cycloalkyl, optionally substituted 3-20 membered heterocyclyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted aryl, and optionally substituted heteroaryl, or
• R26 and R27, together with the atom to which they are connected form an optionally substituted 3-8 membered cycloalkyl or heterocyclyl ring;
• and
• pharmaceutically acceptable salts thereof.

A 5HT2A agonist, comprising a compound having the structure of FORMULA 2A or FORMULA 2B,

• wherein;
• X is selected from N, CH or CR7;
• Y is selected from N or C;
• R1 and R2 at each occurrence, are independently selected from null, hydrogen, halogen, C1-C8 alkyl, oxo, Ph, C(O)R21, C(O)OR21, C(O)NR21R22, S(O)R21, S(O)2R21, S(O)2NR21R22, optionally substituted C1-C8 alkyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted C1-C8 alkoxy, optionally substituted C1-C8alkoxyC1-C8alkyl, optionally substituted C1-C8 alkylaminoC1-C8 alkyl, optionally substituted 3-8 membered cycloalkyl, optionally substituted C3-C8 cycloalkoxy, optionally substituted 3-8 membered heterocyclyl, optionally substituted aryl, and optionally substituted heteroaryl;
• wherein
• R21 and R22 are independently selected from hydrogen, optionally substituted C1-C8 alkyl, optionally substituted C1-C8alkoxyC1-C8alkyl, optionally substituted C1-C8alkylaminoC1-C8alkyl, optionally substituted C3-C10 cycloalkyl, optionally substituted 3-20 membered heterocyclyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted aryl, and optionally substituted heteroaryl, or
• R21 and R22, together with the atom to which they are connected form an optionally substituted 3-8 membered cycloalkyl or heterocyclyl ring;
• R4, R5, R6 and R7 at each occurrence, are independently selected from hydrogen, halogen, C1-C8 alkyl, oxo, Ph, CN, NO2, OR23, SR23, NR23R24, C(O)R23, C(O)OR23, C(O)NR23R24, S(O)R23, S(O)2R13, S(O)2NR23R24, NR25C(O)OR23, NR25C(O)R23, NR25C(O)NR23R24, NR25S(O)R23, NR25S(O)2R13, NR15S(O)2NR13R24, optionally substituted C1-C8 alkyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted C1-C8 alkoxy, optionally substituted C1-C8alkoxyC1-C8 alkyl, optionally substituted C1-C8 alkylaminoC1-C8 alkyl, optionally substituted 3-8 membered cycloalkyl, optionally substituted C3-C8 cycloalkoxy, optionally substituted 3-8 membered heterocyclyl, optionally substituted aryl, and optionally substituted heteroaryl;
• wherein
• R23, R24, and R25 are independently selected from hydrogen, optionally substituted C1-C8 alkyl, optionally substituted C1-C8alkoxyC1-C8alkyl, optionally substituted C1-C8alkylaminoC1-C8alkyl, optionally substituted C3-C10 cycloalkyl, optionally substituted 3-20 membered heterocyclyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted aryl, and optionally substituted heteroaryl, or
• R23 and R24, R23 and R25, R24 and R25 together with the atom to which they are connected form an optionally substituted 3-8 membered cycloalkyl or heterocyclyl ring;
• R8, R9, R10, Ru, R1, R13 and R14, at each occurrence, are independently selected from hydrogen, halogen, C1-C8 alkyl, oxo, Ph, CN, NO2, OR31, SR3, NR31R32, C(O)R31, C(O)OR3, C(O)NR31R32, S(O)R31, S(O)2R31, S(O)2NR31R32, NR33C(O)OR3, NR33C(O)R31, NR33C(O)NR31R32, NR33S(O)R3, NR33S(O)2R3, NR33S(O)2NR31R32, optionally substituted C1-C8 alkyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted C1-C8alkoxy, optionally substituted C1-C8alkoxyC1-C8 alkyl, optionally substituted C1-C8 alkylaminoC1-C8 alkyl, optionally substituted 3-8 membered cycloalkyl, optionally substituted C3-C8 cycloalkoxy, optionally substituted 3-8 membered heterocyclyl, optionally substituted aryl, and optionally substituted heteroaryl;
• wherein
• R31, R32, and R33 are independently selected from hydrogen, optionally substituted C1-C8 alkyl, optionally substituted C1-C8alkoxyC1-C8alkyl, optionally substituted C1-C8alkylaminoC1-C8alkyl, optionally substituted C3-C10 cycloalkyl, optionally substituted 3-20 membered heterocyclyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted aryl, and optionally substituted heteroaryl, or
• R31 and R32, R31 and R33, R32 and R33 together with the atom to which they are connected form an optionally substituted 3-8 membered cycloalkyl or heterocyclyl ring;
• R3 is selected from hydrogen, methyl, ethyl, n-propyl, C1-C8 alkyl, CD3, Ph, C(O)R26, C(O)OR26, C(O)NR26R27, S(O)R26, S(O)2R26, S(O)2NR26R27, optionally substituted C1-C8 alkyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted C1-C8 alkoxy, optionally substituted C1-C8alkoxyC1-C8alkyl, optionally substituted C1-C8alkylaminoC1-C8 alkyl, optionally substituted 3-8 membered cycloalkyl, optionally substituted C3-C8 cycloalkoxy, optionally substituted 3-8 membered heterocyclyl, optionally substituted aryl, and optionally substituted heteroaryl;
• wherein
• R26 and R27 are independently selected from hydrogen, optionally substituted C1-C8alkyl, optionally substituted C1-C8alkoxyC1-C8alkyl, optionally substituted C1-C8alkylaminoC1-C8alkyl, optionally substituted C3-C10 cycloalkyl, optionally substituted 3-20 membered heterocyclyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted aryl, and optionally substituted heteroaryl, or
• R26 and R27, together with the atom to which they are connected form an optionally substituted 3-8 membered cycloalkyl or heterocyclyl ring;
• R15 and R16, at each occurrence, are independently selected from hydrogen, halogen, C1-C8 alkyl, oxo, Ph, CN, N02, OR34, SR34, NR34R35, C(O)R34, C(O)OR34, C(O)NR34R35, S(O)R34, S(O)2R34, S(O)2NR34R35, NR36C(O)OR34, NR36C(O)R34, NR36C(O)NR34R35, NR36S(O)R34, NR36S(O)2R34, NR36S(O)2NR34R35, optionally substituted C1-C8 alkyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted C1-C8 alkoxy, optionally substituted C1-C8alkoxyC1-C8alkyl, optionally substituted C1-C8alkylaminoC1-C8alkyl, optionally substituted 3-8 membered cycloalkyl, optionally substituted C3-C8 cycloalkoxy, optionally substituted 3-8 membered heterocyclyl, optionally substituted aryl, and optionally substituted heteroaryl;
• wherein
• R34, R3, and R36 are independently selected from hydrogen, optionally substituted C1-C8 alkyl, optionally substituted C1-C8alkoxyC1-C8alkyl, optionally substituted C1-C8alkylaminoC1-C8alkyl, optionally substituted C3-C10 cycloalkyl, optionally substituted 3-20 membered heterocyclyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted aryl, and optionally substituted heteroaryl, or
• R34 and R35, R34 and R36, R35 and R36 together with the atom to which they are connected form an optionally substituted 3-8 membered cycloalkyl or heterocyclyl ring;
• optionally, R15 and R16 together with the atom to which they are connected form an optionally substituted 3-8 membered cycloalkyl or heterocyclyl ring;
• and
• pharmaceutically acceptable salts thereof.

A 5HT2A agonist, comprising a compound having the structure of FORMULA 2C or FORMULA 2D,

• wherein,
• X is selected from N, CH or CR7;
• Y is selected from N or C;
• R1 and R2 at each occurrence, are independently selected from null, hydrogen, halogen, C1-C8 alkyl, oxo, Ph, C(O)R21, C(O)OR21, C(O)NR21R22, S(O)R21, S(O)2R21, S(O)2NR21R22, optionally substituted C1-C8 alkyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted C1-C8 alkoxy, optionally substituted C1-C8alkoxyC1-C8 alkyl, optionally substituted C1-C8 alkylaminoC1-C8 alkyl, optionally substituted 3-8 membered cycloalkyl, optionally substituted C3-C8 cycloalkoxy, optionally substituted 3-8 membered heterocyclyl, optionally substituted aryl, and optionally substituted heteroaryl;
• wherein
• R21 and R22 are independently selected from hydrogen, optionally substituted C1-C8 alkyl, optionally substituted C1-C8alkoxyC1-C8alkyl, optionally substituted C1-C8alkylaminoC1-C8alkyl, optionally substituted C3-C10 cycloalkyl, optionally substituted 3-20 membered heterocyclyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted aryl, and optionally substituted heteroaryl, or
• R21 and R22, together with the atom to which they are connected form an optionally substituted 3-8 membered cycloalkyl or heterocyclyl ring;
• R4, R5, R6 and R7 at each occurrence, are independently selected from hydrogen, halogen, C1-C8 alkyl, oxo, Ph, CN, NO2, OR23, SR23, NR23R24, C(O)R23, C(O)OR1, C(O)NR23R24, S(O)R23, S(O)2R23, S(O)2NR23R24, NR25C(O)OR23, NR25C(O)R23, NR25C(O)NR23R24, NR25S(O)R23, NR25S(O)2R23, NR25S(O)2NR23R24, optionally substituted C1-C8 alkyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted C1-C8alkoxy, optionally substituted C1-C8alkoxyC1-C8 alkyl, optionally substituted C1-C8 alkylaminoC1-C8 alkyl, optionally substituted 3-8 membered cycloalkyl, optionally substituted C3-C8 cycloalkoxy, optionally substituted 3-8 membered heterocyclyl, optionally substituted aryl, and optionally substituted heteroaryl;
• wherein
• R23, R24, and R25 are independently selected from hydrogen, optionally substituted C1-C8 alkyl, optionally substituted C1-C8alkoxyC1-C8alkyl, optionally substituted C1-C8alkylaminoC1-C8alkyl, optionally substituted C3-C10 cycloalkyl, optionally substituted 3-20 membered heterocyclyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted aryl, and optionally substituted heteroaryl, or
• R23 and R24, R23 and R25, R24 and R25 together with the atom to which they are connected form an optionally substituted 3-8 membered cycloalkyl or heterocyclyl ring;
• R8, R9, R10, R11, R12, R13 and R14, at each occurrence, are independently selected from hydrogen, halogen, C1-C8 alkyl, oxo, Ph, CN, NO2, OR31, SR31, NR31R32, C(O)R31, C(O)OR31, C(O)NR31R32, S(O)R31, S(O)2R31, S(O)2NR31R32, NR33C(O)OR31, NR33C(O)R31, NR33C(O)NR31R32, NR33S(O)R31, NR33S(O)2R31, NR33S(O)2NR31R32, optionally substituted C1-C8 alkyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted C1-C8alkoxy, optionally substituted C1-C8alkoxyC1-C8 alkyl, optionally substituted C1-C8 alkylaminoC1-C8 alkyl, optionally substituted 3-8 membered cycloalkyl, optionally substituted C3-C8 cycloalkoxy, optionally substituted 3-8 membered heterocyclyl, optionally substituted aryl, and optionally substituted heteroaryl;
• wherein
• R31, R32, and R33 are independently selected from hydrogen, optionally substituted C1-C8 alkyl, optionally substituted C1-C8alkoxyC1-C8alkyl, optionally substituted C1-C8alkylaminoC1-C8alkyl, optionally substituted C3-C10 cycloalkyl, optionally substituted 3-20 membered heterocyclyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted aryl, and optionally substituted heteroaryl, or
• R31 and R32, R31 and R33, R32 and R33 together with the atom to which they are connected form an optionally substituted 3-8 membered cycloalkyl or heterocyclyl ring;
• R3 is selected from hydrogen, methyl, ethyl, n-propyl, C1-C8 alkyl, CD3, Ph, C(O)R26, C(O)OR26, C(O)NR26R27, S(O)R26, S(O)2R26, S(O)2NR26R27, optionally substituted C1-C8 alkyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted C1-C8 alkoxy, optionally substituted C1-C8alkoxyC1-C8alkyl, optionally substituted C1-C8 alkylaminoC1-C8 alkyl, optionally substituted 3-8 membered cycloalkyl, optionally substituted C3-C8 cycloalkoxy, optionally substituted 3-8 membered heterocyclyl, optionally substituted aryl, and optionally substituted heteroaryl;
• wherein
• R26 and R27 are independently selected from hydrogen, optionally substituted C1-C8 alkyl, optionally substituted C1-C8alkoxyC1-C8alkyl, optionally substituted C1-C8alkylaminoC1-C8alkyl, optionally substituted C3-C10 cycloalkyl, optionally substituted 3-20 membered heterocyclyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted aryl, and optionally substituted heteroaryl, or
• R26 and R27, together with the atom to which they are connected form an optionally substituted 3-8 membered cycloalkyl or heterocyclyl ring;
• R15 and R16, at each occurrence, are independently selected from hydrogen, halogen, C1-C8 alkyl, oxo, Ph, CN, NO2, OR34, SR34, NR34R35, C(O)R34, C(O)OR34, C(O)NR34R35, S(O)R34, S(O)2R34, S(O)2NR34R35, NR36C(O)OR34, NR36C(O)R34, NR36C(O)NR34R35, NR36S(O)R34, NR36S(O)2R34, NR36S(O)2NR34R35, optionally substituted C1-C8 alkyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted C1-C8 alkoxy, optionally substituted C1-C8alkoxyC1-C8 alkyl, optionally substituted C1-C8 alkylaminoC1-C8 alkyl, optionally substituted 3-8 membered cycloalkyl, optionally substituted C3-C8 cycloalkoxy, optionally substituted 3-8 membered heterocyclyl, optionally substituted aryl, and optionally substituted heteroaryl;
• wherein
• R34, and R35, and R36 are independently selected from hydrogen, optionally substituted C1-C8 alkyl, optionally substituted C1-C8alkoxyC1-C8alkyl, optionally substituted C1-C8alkylaminoC1-C8alkyl, optionally substituted C3-C10 cycloalkyl, optionally substituted 3-20 membered heterocyclyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted aryl, and optionally substituted heteroaryl, or
• R34 and R35, R34 and R36, R35 and R36 together with the atom to which they are connected form an optionally substituted 3-8 membered cycloalkyl or heterocyclyl ring;
• optionally, R15 and R16 together with the atom to which they are connected form an optionally substituted 3-8 membered cycloalkyl or heterocyclyl ring;
• and
• pharmaceutically acceptable salts thereof.

A 5HT2A agonist, comprising a compound having the structure of FORMULA 2E or FORMULA 2F

• wherein,
• X is selected from N, CH or CR7;
• Y is selected from N or C;
• R1 and R2 at each occurrence, are independently selected from null, hydrogen, halogen, C1-C8 alkyl, oxo, Ph, C(O)R21, C(O)OR21, C(O)NR21R22, S(O)R21, S(O)2R21, S(O)2NR21R22, optionally substituted C1-C8 alkyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted C1-C8 alkoxy, optionally substituted C1-C8alkoxyC1-C8 alkyl, optionally substituted C1-C8 alkylaminoC1-C8 alkyl, optionally substituted 3-8 membered cycloalkyl, optionally substituted C3-C8 cycloalkoxy, optionally substituted 3-8 membered heterocyclyl, optionally substituted aryl, and optionally substituted heteroaryl;
• wherein
• R21 and R22 are independently selected from hydrogen, optionally substituted C1-C8 alkyl, optionally substituted C1-C8alkoxyC1-C8alkyl, optionally substituted C1-C8alkylaminoC1-C8alkyl, optionally substituted C3-C10 cycloalkyl, optionally substituted 3-20 membered heterocyclyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted aryl, and optionally substituted heteroaryl, or
• R21 and R22, together with the atom to which they are connected form an optionally substituted 3-8 membered cycloalkyl or heterocyclyl ring;
• R4, R5, R6 and R7 at each occurrence, are independently selected from hydrogen, halogen, C1-C8 alkyl, oxo, Ph, CN, NO2, OR23, SR23, NR23R24, C(O)R23, C(O)OR23, C(O)NR23R24, S(O)R23, S(O)2R13, S(O)2NR23R24, NR25C(O)OR23, NR25C(O)R23, NR25C(O)NR23R24, NR25S(O)R23, NR25S(O)2R23, NR25S(O)2NR23R24, optionally substituted C1-C8 alkyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted C1-C8 alkoxy, optionally substituted C1-C8alkoxyC1-C8 alkyl, optionally substituted C1-C8 alkylaminoC1-C8 alkyl, optionally substituted 3-8 membered cycloalkyl, optionally substituted C3-C8 cycloalkoxy, optionally substituted 3-8 membered heterocyclyl, optionally substituted aryl, and optionally substituted heteroaryl;
• wherein
• R23, R24, and R25 are independently selected from hydrogen, optionally substituted C1-C8 alkyl, optionally substituted C1-C8alkoxyC1-C8alkyl, optionally substituted C1-C8alkylaminoC1-C8alkyl, optionally substituted C3-C10 cycloalkyl, optionally substituted 3-20 membered heterocyclyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted aryl, and optionally substituted heteroaryl, or
• R23 and R24, R23 and R25, R24 and R25 together with the atom to which they are connected form an optionally substituted 3-8 membered cycloalkyl or heterocyclyl ring;
• R8, R9, R10, R11, R12, R13 and R14, at each occurrence, are independently selected from hydrogen, halogen, C1-C8 alkyl, oxo, Ph, CN, NO2, OR31, SR31, NR31R32, C(O)R31, C(O)OR31, C(O)NR31R32, S(O)R31, S(O)2R31, S(O)2NR31R32, NR33C(O)OR3, NR33C(O)R31, NR33C(O)NR31R32, NR33S(O)R31, NR33S(O)2R31, NR33S(O)2NR31R32, optionally substituted C1-C8 alkyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted C1-C8 alkoxy, optionally substituted C1-C8alkoxyC1-C8alkyl, optionally substituted C1-C8alkylaminoC1-C8 alkyl, optionally substituted 3-8 membered cycloalkyl, optionally substituted C3-C8 cycloalkoxy, optionally substituted 3-8 membered heterocyclyl, optionally substituted aryl, and optionally substituted heteroaryl;
• wherein
• R31, R32, and R33 are independently selected from hydrogen, optionally substituted C1-C8 alkyl, optionally substituted C1-C8alkoxyC1-C8alkyl, optionally substituted C1-C8alkylaminoC1-C8alkyl, optionally substituted C3-C10 cycloalkyl, optionally substituted 3-20 membered heterocyclyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted aryl, and optionally substituted heteroaryl, or
• R31 and R32, R31 and R33, R32 and R33 together with the atom to which they are connected form an optionally substituted 3-8 membered cycloalkyl or heterocyclyl ring;
• R3 is selected from hydrogen, methyl, ethyl, n-propyl, C1-C8alkyl, CD3, Ph, C(O)R26, C(O)OR26, C(O)NR26R27, S(O)R26, S(O)2R26, S(O)2NR26R27, optionally substituted C1-C8 alkyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted C1-C8 alkoxy, optionally substituted C1-C8alkoxyC1-C8alkyl, optionally substituted C1-C8alkylaminoC1-C8 alkyl, optionally substituted 3-8 membered cycloalkyl, optionally substituted C3-C8 cycloalkoxy, optionally substituted 3-8 membered heterocyclyl, optionally substituted aryl, and optionally substituted heteroaryl;
• wherein
• R26 and R27 are independently selected from hydrogen, optionally substituted C1-C8alkyl, optionally substituted C1-C8alkoxyC1-C8alkyl, optionally substituted C1-C8alkylaminoC1-C8alkyl, optionally substituted C3-C10 cycloalkyl, optionally substituted 3-20 membered heterocyclyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted aryl, and optionally substituted heteroaryl, or
• R26 and R27, together with the atom to which they are connected form an optionally substituted 3-8 membered cycloalkyl or heterocyclyl ring;
• R15 and R16, at each occurrence, are independently selected from hydrogen, halogen, C1-C8 alkyl, oxo, Ph, CN, NO2, OR34, SR34, NR34R35, C(O)R34, C(O)OR34, C(O)NR34R35, S(O)R34, S(O)2R34, S(O)2NR34R35, NR36C(O)OR34, NR36C(O)R34, NR36C(O)NR34R35, NR36S(O)R34, NR36S(O)2R34, NR36S(O)2NR34R35, optionally substituted C1-C8 alkyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted C1-C8alkoxy, optionally substituted C1-C8alkoxyC1-C8alkyl, optionally substituted C1-C8 alkylaminoC1-C8 alkyl, optionally substituted 3-8 membered cycloalkyl, optionally substituted C3-C8 cycloalkoxy, optionally substituted 3-8 membered heterocyclyl, optionally substituted aryl, and optionally substituted heteroaryl;
• wherein
• R34, and R35, and R36 are independently selected from hydrogen, optionally substituted C1-C8 alkyl, optionally substituted C1-C8alkoxyC1-C8alkyl, optionally substituted C1-C8alkylaminoC1-C8alkyl, optionally substituted C3-C10 cycloalkyl, optionally substituted 3-20 membered heterocyclyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted aryl, and optionally substituted heteroaryl, or
• R34 and R35, R34 and R36, R35 and R36 together with the atom to which they are connected form an optionally substituted 3-8 membered cycloalkyl or heterocyclyl ring;
• optionally, R15 and R16 together with the atom to which they are connected form an optionally substituted 3-8 membered cycloalkyl or heterocyclyl ring;
• R19 and R20, at each occurrence, are independently selected from hydrogen, halogen, C1-C8 alkyl, oxo, Ph, CN, NO2, OR37, SR37, NR37R38, C(O)R37, C(O)OR38, C(O)NR37R38, S(O)R37, S(O)2R37, S(O)2NR37R38, NR39C(O)OR37, NR39C(O)R37, NR39C(O)NR37R38, NR39S(O)R37, NR39S(O)2R37, NR36S(O)2NR37R38, optionally substituted C1-C8 alkyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted C1-C8 alkoxy, optionally substituted C1-C8alkoxyC1-C8alkyl, optionally substituted C1-C8 alkylaminoC1-C8alkyl, optionally substituted 3-8 membered cycloalkyl, optionally substituted C3-C8 cycloalkoxy, optionally substituted 3-8 membered heterocyclyl, optionally substituted aryl, and optionally substituted heteroaryl;
• wherein
• R37, R38, and R39 are independently selected from hydrogen, optionally substituted C1-C8 alkyl, optionally substituted C1-C8alkoxyC1-C8alkyl, optionally substituted C1-C8alkylaminoC1-C8alkyl, optionally substituted C3-C10 cycloalkyl, optionally substituted 3-20 membered heterocyclyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted aryl, and optionally substituted heteroaryl, or
• R37 and R38, R37 and R39, R38 and R39 together with the atom to which they are connected form an optionally substituted 3-8 membered cycloalkyl or heterocyclyl ring;
• and
• pharmaceutically acceptable salts thereof.

A 5HT2A agonist, comprising a compound having the structure of FORMULA 3

• wherein;
• X is selected from N, CH or CR7;
• Y is selected from N or C;
• R1 and R2 at each occurrence, are independently selected from null, hydrogen, halogen, C1-C8 alkyl, oxo, Ph, C(O)R21, C(O)OR21, C(O)NR21R22, S(O)R21, S(O)2R21, S(O)2NR21R22, optionally substituted C1-C8 alkyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted C1-C8 alkoxy, optionally substituted C1-C8alkoxyC1-C8 alkyl, optionally substituted C1-C8 alkylaminoC1-C8 alkyl, optionally substituted 3-8 membered cycloalkyl, optionally substituted C3-C8 cycloalkoxy, optionally substituted 3-8 membered heterocyclyl, optionally substituted aryl, and optionally substituted heteroaryl;
• wherein
• R21 and R22 are independently selected from hydrogen, optionally substituted C1-C8 alkyl, optionally substituted C1-C8alkoxyC1-C8alkyl, optionally substituted C1-C8alkylaminoC1-C8alkyl, optionally substituted C3-C10 cycloalkyl, optionally substituted 3-20 membered heterocyclyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted aryl, and optionally substituted heteroaryl, or
• R21 and R22, together with the atom to which they are connected form an optionally substituted 3-8 membered cycloalkyl or heterocyclyl ring;
• R4, R5, R6 and R7 at each occurrence, are independently selected from hydrogen, halogen, C1-C8 alkyl, oxo, Ph, CN, NO2, OR23, SR23, NR23R24, C(O)R23, C(O)OR23, C(O)NR23R24, S(O)R23, S(O)2R23, S(O)2NR23R24, NR25C(O)OR23, NR25C(O)R23, NR25C(O)NR23R24, NR25S(O)R23, NR25S(O)2R23, NR25S(O)2NR23R24, optionally substituted C1-C8 alkyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted C1-C8 alkoxy, optionally substituted C1-C8alkoxyC1-C8 alkyl, optionally substituted C1-C8 alkylaminoC1-C8 alkyl, optionally substituted 3-8 membered cycloalkyl, optionally substituted C3-C8 cycloalkoxy, optionally substituted 3-8 membered heterocyclyl, optionally substituted aryl, and optionally substituted heteroaryl;
• wherein
• R23, R24, and R25 are independently selected from hydrogen, optionally substituted C1-C8 alkyl, optionally substituted C1-C8alkoxyC1-C8alkyl, optionally substituted C1-C8alkylaminoC1-C8alkyl, optionally substituted C3-C10 cycloalkyl, optionally substituted 3-20 membered heterocyclyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted aryl, and optionally substituted heteroaryl, or
• R23 and R24, R23 and R25, R24 and R25 together with the atom to which they are connected form an optionally substituted 3-8 membered cycloalkyl or heterocyclyl ring;
• R3 is selected from hydrogen, methyl, ethyl, n-propyl, C1-C8 alkyl, CD3, Ph, C(O)R26, C(O)OR26, C(O)NR26R27, S(O)R26, S(O)2R26, S(O)2NR26R27, optionally substituted C1-C8 alkyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted C1-C8 alkoxy, optionally substituted C1-C8alkoxyC1-C8 alkyl, optionally substituted C1-C8 alkylaminoC1-C8 alkyl, optionally substituted 3-8 membered cycloalkyl, optionally substituted C3-C8 cycloalkoxy, optionally substituted 3-8 membered heterocyclyl, optionally substituted aryl, and optionally substituted heteroaryl;
• wherein
• R26 and R27 are independently selected from hydrogen, optionally substituted C1-C8alkyl, optionally substituted C1-C8alkoxyC1-C8alkyl, optionally substituted C1-C8alkylaminoC1-C8alkyl, optionally substituted C3-C10 cycloalkyl, optionally substituted 3-20 membered heterocyclyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted aryl, and optionally substituted heteroaryl, or
• R26 and R27, together with the atom to which they are connected form an optionally substituted 3-8 membered cycloalkyl or heterocyclyl ring;
• and
• R17 and R18 at each occurrence, are independently selected from hydrogen, halogen, C1-C8alkyl, oxo, Ph, CN, NO2, OR28, SR28, NR28R29, C(O)R28, C(O)OR29, C(O)NR28R29, S(O)R28, S(O)2R28, S(O)2NR28R29, NR30C(O)OR28, NR30C(O)R28, NR30C(O)NR28R29, NR30S(O)R28, NR30S(O)2R28, NR30S(O)2NR28R29, optionally substituted C1-C8 alkyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted C1-C8 alkoxy, optionally substituted C1-C8alkoxyC1-C8alkyl, optionally substituted C1-C8 alkylaminoC1-C8 alkyl, optionally substituted 3-8 membered cycloalkyl, optionally substituted C3-C8 cycloalkoxy, optionally substituted 3-8 membered heterocyclyl, optionally substituted aryl, and optionally substituted heteroaryl;
• wherein;
• R28, R29, and R30 are independently selected from hydrogen, optionally substituted C1-C8 alkyl, optionally substituted C1-C8alkoxyC1-C8alkyl, optionally substituted C1-C8alkylaminoC1-C8alkyl, optionally substituted C3-C10 cycloalkyl, optionally substituted 3-20 membered heterocyclyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted aryl, and optionally substituted heteroaryl, or
• R28 and R29, R28 and R30, R29 and R30 together with the atom to which they are connected form an optionally substituted 3-20 membered cycloalkyl or heterocyclyl ring;
• R8, R9, R10, R11, R12, R13 and R14, at each occurrence, are independently selected from hydrogen, halogen, C1-C8 alkyl, oxo, Ph, CN, NO2, OR31, SR31, NR31R32, C(O)R31, C(O)OR31, C(O)NR31R32, S(O)R31, S(O)2R31, S(O)2NR31R32, NR33C(O)OR31, NR33C(O)R31, NR33C(O)NR31R32, NR33S(O)R31, NR33S(O)2R31, NR33S(O)2NR31R32, optionally substituted C1-C8 alkyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted C1-C8 alkoxy, optionally substituted C1-C8alkoxyC1-C8 alkyl, optionally substituted C1-C8 alkylaminoC1-C8 alkyl, optionally substituted 3-8 membered cycloalkyl, optionally substituted C3-C8 cycloalkoxy, optionally substituted 3-8 membered heterocyclyl, optionally substituted aryl, and optionally substituted heteroaryl;
• wherein
• R31, R32, and R33 are independently selected from hydrogen, optionally substituted C1-C8 alkyl, optionally substituted C1-C8alkoxyC1-C8alkyl, optionally substituted C1-C8alkylaminoC1-C8alkyl, optionally substituted C3-C10 cycloalkyl, optionally substituted 3-20 membered heterocyclyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted aryl, and optionally substituted heteroaryl, or
• R39 and R32, R39 and R33, R32 and R33 together with the atom to which they are connected form an optionally substituted 3-8 membered cycloalkyl or heterocyclyl ring;
• and
• pharmaceutically acceptable salts thereof.

A 5HT2A agonist, comprising a compound having the structure of FORMULA 4

• wherein;
• X is selected from N, CH or CR7;
• Y is selected from N or C;
• R1 and R2 at each occurrence, are independently selected from null, hydrogen, halogen, C1-C8 alkyl, oxo, Ph, C(O)R21, C(O)OR21, C(O)NR21R22, S(O)R21, S(O)2R21, S(O)2NR21R22, optionally substituted C1-C8 alkyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted C1-C8 alkoxy, optionally substituted C1-C8alkoxyC1-C8 alkyl, optionally substituted C1-C8 alkylaminoC1-C8 alkyl, optionally substituted 3-8 membered cycloalkyl, optionally substituted C3-C8 cycloalkoxy, optionally substituted 3-8 membered heterocyclyl, optionally substituted aryl, and optionally substituted heteroaryl;
• wherein
• R21 and R22 are independently selected from hydrogen, optionally substituted C1-C8 alkyl, optionally substituted C1-C8alkoxyC1-C8alkyl, optionally substituted C1-C8alkylaminoC1-C8alkyl, optionally substituted C3-C10 cycloalkyl, optionally substituted 3-20 membered heterocyclyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted aryl, and optionally substituted heteroaryl, or
• R21 and R22, together with the atom to which they are connected form an optionally substituted 3-8 membered cycloalkyl or heterocyclyl ring;
• R4, R5, R6 and R7 at each occurrence, are independently selected from hydrogen, halogen, C1-C8 alkyl, oxo, Ph, CN, NO2, OR23, SR23, NR23R24, C(O)R23, C(O)OR23, C(O)NR23R24, S(O)R23, S(O)2R23, S(O)2NR23R24, NR25C(O)OR23, NR25C(O)R23, NR25C(O)NR23R24, NR25S(O)R23, NR25S(O)2R23, NR25S(O)2NR23R24, optionally substituted C1-C8 alkyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted C1-C8alkoxy, optionally substituted C1-C8alkoxyC1-C8 alkyl, optionally substituted C1-C8 alkylaminoC1-C8 alkyl, optionally substituted 3-8 membered cycloalkyl, optionally substituted C3-C8 cycloalkoxy, optionally substituted 3-8 membered heterocyclyl, optionally substituted aryl, and optionally substituted heteroaryl;
• wherein
• R23, R24, and R25 are independently selected from hydrogen, optionally substituted C1-C8 alkyl, optionally substituted C1-C8alkoxyC1-C8alkyl, optionally substituted C1-C8alkylaminoC1-C8alkyl, optionally substituted C3-C10 cycloalkyl, optionally substituted 3-20 membered heterocyclyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted aryl, and optionally substituted heteroaryl, or
• R23 and R24, R23 and R25, R24 and R25 together with the atom to which they are connected form an optionally substituted 3-8 membered cycloalkyl or heterocyclyl ring;
• R3 is selected from hydrogen, methyl, ethyl, n-propyl, C1-C8 alkyl, CD3, Ph, C(O)R26, C(O)OR26, C(O)NR26R27, S(O)R26, S(O)2R26, S(O)2NR26R27, optionally substituted C1-C8 alkyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted C1-C8 alkoxy, optionally substituted C1-C8alkoxyC1-C8 alkyl, optionally substituted C1-C8 alkylaminoC1-C8 alkyl, optionally substituted 3-8 membered cycloalkyl, optionally substituted C3-C8 cycloalkoxy, optionally substituted 3-8 membered heterocyclyl, optionally substituted aryl, and optionally substituted heteroaryl;
• wherein
• R26 and R27 are independently selected from hydrogen, optionally substituted C1-C8 alkyl, optionally substituted C1-C8alkoxyC1-C8alkyl, optionally substituted C1-C8alkylaminoC1-C8alkyl, optionally substituted C3-C10 cycloalkyl, optionally substituted 3-20 membered heterocyclyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted aryl, and optionally substituted heteroaryl, or
• R26 and R27, together with the atom to which they are connected form an optionally substituted 3-8 membered cycloalkyl or heterocyclyl ring;
• and
• R17 and R18 at each occurrence, are independently selected from hydrogen, halogen, C1-C8alkyl, oxo, Ph, CN, NO2, OR28, SR28, NR28R29, C(O)R28, C(O)OR29, C(O)NR28R29, S(O)R28, S(O)2R28, S(O)2NR28R29, NR30C(O)OR28, NR30C(O)R28, NR30C(O)NR28R29, NR30S(O)R28, NR30S(O)2R28, NR30S(O)2NR28R29, optionally substituted C1-C8alkyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted C1-C8 alkoxy, optionally substituted C1-C8alkoxyC1-C8alkyl, optionally substituted C1-C8alkylaminoC1-C8alkyl, optionally substituted 3-8 membered cycloalkyl, optionally substituted C3-C8 cycloalkoxy, optionally substituted 3-8 membered heterocyclyl, optionally substituted aryl, and optionally substituted heteroaryl;
• wherein;
• R28, R29, and R30 are independently selected from hydrogen, optionally substituted C1-C8alkyl, optionally substituted C1-C8alkoxyC1-C8alkyl, optionally substituted C1-C8alkylaminoC1-C8alkyl, optionally substituted C3-C10 cycloalkyl, optionally substituted 3-20 membered heterocyclyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted aryl, and optionally substituted heteroaryl, or
• R28 and R29, R28 and R30, R29 and R30 together with the atom to which they are connected form an optionally substituted 3-20 membered cycloalkyl or heterocyclyl ring;
• R10, R11, R12, R13 and R14, at each occurrence, are independently selected from hydrogen, halogen, C1-C8 alkyl, oxo, Ph, CN, NO2, OR31, SR31, NR31R32, C(O)R31, C(O)OR31, C(O)NR31R32, S(O)R31, S(O)2R31, S(O)2NR31R32, NR33C(O)OR31, NR33C(O)R31, NR33C(O)NR31R32, NR33S(O)R31, NR33S(O)2R31, NR33S(O)2NR31R31, optionally substituted C1-C8 alkyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted C1-C8alkoxy, optionally substituted C1-C8alkoxyC1-C8alkyl, optionally substituted C1-C8 alkylaminoC1-C8 alkyl, optionally substituted 3-8 membered cycloalkyl, optionally substituted C3-C8 cycloalkoxy, optionally substituted 3-8 membered heterocyclyl, optionally substituted aryl, and optionally substituted heteroaryl;
• wherein
• R31, R32, and R33 are independently selected from hydrogen, optionally substituted C1-C8 alkyl, optionally substituted C1-C8alkoxyC1-C8alkyl, optionally substituted C1-C8alkylaminoC1-C8alkyl, optionally substituted C3-C10 cycloalkyl, optionally substituted 3-20 membered heterocyclyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted aryl, and optionally substituted heteroaryl, or
• R31 and R32, R31 and R33, R32 and R33 together with the atom to which they are connected form an optionally substituted 3-8 membered cycloalkyl or heterocyclyl ring;
• and
• pharmaceutically acceptable salts thereof.

A 5HT2A agonist, comprising a compound having the structure of FORMULA 5

• wherein;
• X is selected from N, CH or CR7;
• Y is selected from N or C;
• R1 and R2 at each occurrence, are independently selected from null, hydrogen, halogen, C1-C8 alkyl, oxo, Ph, C(O)R21, C(O)OR21, C(O)NR21R22, S(O)R21, S(O)2R21, S(O)2NR21R22, optionally substituted C1-C8 alkyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted C1-C8 alkoxy, optionally substituted C1-C8alkoxyC1-C8 alkyl, optionally substituted C1-C8 alkylaminoC1-C8 alkyl, optionally substituted 3-8 membered cycloalkyl, optionally substituted C3-C8 cycloalkoxy, optionally substituted 3-8 membered heterocyclyl, optionally substituted aryl, and optionally substituted heteroaryl;
• wherein
• R21 and R22 are independently selected from hydrogen, optionally substituted C1-C8 alkyl, optionally substituted C1-C8alkoxyC1-C8alkyl, optionally substituted C1-C8alkylaminoC1-C8alkyl, optionally substituted C3-C10 cycloalkyl, optionally substituted 3-20 membered heterocyclyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted aryl, and optionally substituted heteroaryl, or
• R21 and R22, together with the atom to which they are connected form an optionally substituted 3-8 membered cycloalkyl or heterocyclyl ring;
• R4, R5, R6 and R7 at each occurrence, are independently selected from hydrogen, halogen, C1-C8 alkyl, oxo, Ph, CN, NO2, OR23, SR23, NR23R24, C(O)R23, C(O)OR23, C(O)NR23R24, S(O)R23, S(O)2R13, S(O)2NR23R24, NR25C(O)OR23, NR25C(O)R23, NR25C(O)NR23R24, NR25S(O)R23, NR25S(O)2R23, NR25S(O)2NR23R24, optionally substituted C1-C8 alkyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted C1-C8 alkoxy, optionally substituted C1-C8alkoxyC1-C8 alkyl, optionally substituted C1-C8 alkylaminoC1-C8 alkyl, optionally substituted 3-8 membered cycloalkyl, optionally substituted C3-C8 cycloalkoxy, optionally substituted 3-8 membered heterocyclyl, optionally substituted aryl, and optionally substituted heteroaryl;
• wherein
• R23, R24, and R25 are independently selected from hydrogen, optionally substituted C1-C8 alkyl, optionally substituted C1-C8alkoxyC1-C8alkyl, optionally substituted C1-C8alkylaminoC1-C8alkyl, optionally substituted C3-C10 cycloalkyl, optionally substituted 3-20 membered heterocyclyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted aryl, and optionally substituted heteroaryl, or
• R23 and R24, R23 and R25, R24 and R25 together with the atom to which they are connected form an optionally substituted 3-8 membered cycloalkyl or heterocyclyl ring;
• R3 is selected from hydrogen, methyl, ethyl, n-propyl, C1-C8 alkyl, CD3, Ph, C(O)R26, C(O)OR26, C(O)NR26R27, S(O)R26, S(O)2R26, S(O)2NR26R27, optionally substituted C1-C8 alkyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted C1-C8 alkoxy, optionally substituted C1-C8alkoxyC1-C8alkyl, optionally substituted C1-C8 alkylaminoC1-C8 alkyl, optionally substituted 3-8 membered cycloalkyl, optionally substituted C3-C8 cycloalkoxy, optionally substituted 3-8 membered heterocyclyl, optionally substituted aryl, and optionally substituted heteroaryl;
• wherein
• R26 and R27 are independently selected from hydrogen, optionally substituted C1-C8 alkyl, optionally substituted C1-C8alkoxyC1-C8alkyl, optionally substituted C1-C8alkylaminoC1-C8alkyl, optionally substituted C3-C10 cycloalkyl, optionally substituted 3-20 membered heterocyclyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted aryl, and optionally substituted heteroaryl, or
• R26 and R27, together with the atom to which they are connected form an optionally substituted 3-8 membered cycloalkyl or heterocyclyl ring;
• and
• R10, R11, R12 and R13, at each occurrence, are independently selected from hydrogen, halogen, C1-C8 alkyl, oxo, Ph, CN, NO2, OR31, SR31, NR31R32, C(O)R31, C(O)OR31, C(O)NR31R32, S(O)R31, S(O)2R31, S(O)2NR31R32, NR33C(O)OR31, NR33C(O)R31, NR33C(O)NR31R32, NR33S(O)R31, NR33S(O)2R3, NR33S(O)2NR31R32, optionally substituted C1-C8 alkyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted C1-C8alkoxy, optionally substituted C1-C8alkoxyC1-C8alkyl, optionally substituted C1-C8 alkylaminoC1-C8alkyl, optionally substituted 3-8 membered cycloalkyl, optionally substituted C3-C8 cycloalkoxy, optionally substituted 3-8 membered heterocyclyl, optionally substituted aryl, and optionally substituted heteroaryl;
• wherein
• R31, R32, and R33 are independently selected from hydrogen, optionally substituted C1-C8 alkyl, optionally substituted C1-C8alkoxyC1-C8alkyl, optionally substituted C1-C8alkylaminoC1-C8alkyl, optionally substituted C3-C10 cycloalkyl, optionally substituted 3-20 membered heterocyclyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted aryl, and optionally substituted heteroaryl, or
• R31 and R32, R31 and R33, R32 and R33 together with the atom to which they are connected form an optionally substituted 3-8 membered cycloalkyl or heterocyclyl ring;
• R16, at each occurrence, is independently selected from hydrogen, halogen, C1-C8 alkyl, oxo, Ph, CN, NO2, OR34, SR34, NR34R35, C(O)R34, C(O)OR34, C(O)NR34R35, S(O)R34, S(O)2R34, S(O)2NR34R35, NR36C(O)OR34, NR36C(O)R34, NR36C(O)NR34R35, NR36S(O)R34, NR36S(O)2R34, NR36S(O)2NR34R35, optionally substituted C1-C8 alkyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted C1-C8 alkoxy, optionally substituted C1-C8alkoxyC1-C8 alkyl, optionally substituted C1-C8 alkylaminoC1-C8 alkyl, optionally substituted 3-8 membered cycloalkyl, optionally substituted C3-C8 cycloalkoxy, optionally substituted 3-8 membered heterocyclyl, optionally substituted aryl, and optionally substituted heteroaryl;
• wherein
• R34, and R35, and R36 are independently selected from hydrogen, optionally substituted C1-C8 alkyl, optionally substituted C1-C8alkoxyC1-C8alkyl, optionally substituted C1-C8alkylaminoC1-C8alkyl, optionally substituted C3-C10 cycloalkyl, optionally substituted 3-20 membered heterocyclyl, optionally substituted C2-C8 alkenyl, optionally substituted C2-C8 alkynyl, optionally substituted aryl, and optionally substituted heteroaryl, or
• R34 and R35, R34 and R36, R35 and R36 together with the atom to which they are connected form an optionally substituted 3-8 membered cycloalkyl or heterocyclyl ring;
• and pharmaceutically acceptable salts thereof.

A 5HT2A agonist comprising a compound selected from the group consisting of:

• NS131-179, NS131-178, NS131-177, NS136-006, NS131-169, NS131-168, NS131-167, NS131-173, NS131-180, RS134-52, RS134-48, NS131-185, NS131-170, RS134-45, RS134-40, NS131-184, RS134-49, RS134-53, RS134-41, RS134-46, NS131-172, RS134-38, RS134-65, RS134-62, RS134-70, NS136-081, RS134-73, RS134-72, NS136-092, NS136-091, NS136-096, NS136-095, NS136-102, NS136-101, NS136-115, NS136-116, NS136-117, NS136-118, NS136-119, NS136-120, NS136-109, NS136-110, NS136-111, NS136-112, RS134-37, RS134-56, NS136-002, NS136-004, RS130-132, YX129-177C, YX129-180C, YX143-19, YX143-20, YX143-2, YX143-21, NS144-042, NS144-043, NS144-044, YS135-44, YS135-45, YS135-34, YS135-32, YS135-38, YS135-41, YS135-39, YX143-14A-2, NS144-019, NS144-021, YX143-15, YX143-16, YX143-17C, YX143-18C, NS144-047, NS144-048, NS144-049, NS136-128, NS136-129, NS136-130, NS136-131, NS136-150, NS136-151, NS136-152, NS136-166, NS144-011, NS136-158, NS136-167, NS136-159, NS136-135, NS136-136, NS136-137, NS144-046, NS144-045, NS136-140, NS136-141, NS136-142, NS136-143, NS136-153, NS136-154, NS136-155, NS136-175, NS144-016, NS136-160, NS136-176, NS136-161, NS136-144, NS136-145, NS136-146, NS144-051, NS144-050, YX143-41C, YX143-42C, YX143-43D, NS144-059-2, NS144-054-2, NS144-067, NS144-085, NS144-093, NS144-094, NS144-095, NS144-096, XQ148-012, XQ148-023, ZX147-015, ZX147-016, ZX147-017, ZX147-019, NS144-097, NS144-098, NS144-102, NS144-101, NS144-107, NS144-108, NS144-109, NS144-110, YS135-52, YS135-53, YS135-54, YS135-80, YS135-81, YS135-82, YS135-96, YS135-98, YS135-99, YS135-100, ZX147-026-01, ZX147-026-02, ZX147-027, ZX147-028, ZX147-029, ZX147-031, ZX147-054, ZX147-055, ZX147-056, ZX147-092, ZX147-093, ZX147-094, ZX147-095, ZX147-096, ZX147-097, ZX147-098, ZX147-099, ZX147-100, ZX147-128, ZX147-129, ZX147-130, ZX147-131, ZX147-137, ZX147-183, ZX156-011, ZX156-012, ZX156-014-1, ZX156-014-2, ZX156-019, ZX156-059, ZX156-069, ZX156-070, ZX156-071, ZX156-089, ZX156-090, ZX162-100, ZX162-031, ZX162-104, ZX162-105, ZX162-110, ZX162-111, ZX162-112, ZX162-113, ZX162-124, ZX162-126, ZX162-127, ZX162-128, ZX162-129, ZX162-138, ZX162-139, ZX162-140, ZX162-141, ZX162-147, ZX162-148, ZX162-151, ZX162-173, ZX162-174, ZX162-175, ZX162-176, YX143-103B, YX143-103C, YX143-105C, YX143-108, YX143-110B, YX143-112B, YX143-129, YX143-134C, YX143-138C, YX143-182C-1, YX143-183A, YX143-184B-1, YX143-184B-2, YX143-185B, YX143-186B, YX157-19A, YX157-20A, YX157-29B, YX157-42B, YX157-51B, YX157-51C, YX157-55A, XS159-153, XS159-155, XS159-160, XS159-163, XS159-180, XS159-186, XS165-3, XS165-5, XS165-8, XQ148-93, XQ158-012, XQ158-055, XQ158-056, XQ158-078, XQ158-093A, XQ158-082, XQ158-115, XQ158-164, XQ158-167, XQ158-168, ZD160-34, ZD160-140, ZD160-141, ZD160-149, ZD160-11, ZD160-133, ZD160-130, ZD160-131, QC166-005, QC166-008, QC-166-032, XQ148-86, QC166-096, QC166-097, QC179-001, QC179-002, QC179-025, QC-179-032, QC-179-033, QC179-038, QC179-039, QC179-040, ZX167-072, ZX167-077, ZX167-074, ZX167-090, ZX167-091, ZX162-100-1 (Enantiomer 1 of ZX162-100), ZX162-100-2 (Enantiomer 2 of ZX162-100), ZX162-031-1 (Enantiomer 1 of ZX162-031), ZX162-031-2 (Enantiomer 2 of ZX162-031), ZX167-074-1 (Enantiomer 1 of ZX167-074), ZX167-074-2 (Enantiomer 2 of ZX167-074), ZX177-057, ZX177-058, ZX177-058BY, ZX177-059 and ZX177-060 and pharmaceutically acceptable salts thereof.

A 5HT2A agonist comprising a compound selected from the group consisting of:

• 3-(3-azabicyclo[4.1.0]heptan-1-yl)-7-chloro-1H-indazole (ZX162-031);
• 3-(3-azabicyclo[3.1.0]hexan-1-yl)-7-chloro-1H-indazole (ZX162-100);
• 3-(3-azabicyclo[3.1.0]hexan-1-yl)-7-chloro-1H-indole (ZX167-074);
• and
• 3-(3-azabicyclo[3.1.0]hexan-1-yl)-7-methyl-1H-indole (ZX167-091) and enantiomers, pharmaceutically acceptable salts, solvent complexes, morphological forms, and deuterated and fluorinated derivatives thereof.