# US 12,006,290 B2 · Crystalline norpsilocin compounds

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- Number: US 12,006,290 B2
- Document ID: US12006290B2
- Status: Granted
- Kind: B2
- Application number: 17/906,575
- Filed: 2021-03-18
- Published: 2023-04-13
- Granted: 2024-06-11
- Earliest claimed: 2020-03-19
- Assignees: Caamtech, Inc.
- Applicants: Caamtech, Inc.
- Inventors: Andrew R. Chadeayne
- Web page: https://patentgrep.com/patent/US12006290B2

## CPC

- C07D 209/16: Tryptamines
- A61K 31/01: Hydrocarbons
- A61K 31/4045: Indole-alkylamines; Amides thereof, e.g. serotonin, melatonin
- A61K 31/675: having nitrogen as a ring hetero atom, e.g. pyridoxal phosphate
- A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 25/18: Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- C07C 57/15: Fumaric acid
- C07B 2200/13: Crystalline forms, e.g. polymorphs
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)

## Abstract

The disclosure relates to norpsilocin compounds, compositions containing those crystalline compounds, and methods of treatment using them. The norpsilocin compounds include crystalline 4-hydroxy-N-methyltryptamine (“crystalline 4-HO-NMT” or “crystalline norpsilocin freebase”), crystalline 4-hydroxy-N-methyltryptammonium fumarate (“crystalline norpsilocin fumarate”), and 4-hydroxy-N-methyltryptammonium fumarate (“norpsilocin fumarate”) and their compositions and uses.

## Claims

### Claim 1

A composition comprising crystalline 4-hydroxy-N-methyltryptammonium fumarate (norpsilocin fumarate) and an excipient,
wherein crystalline norpsilocin fumarate is characterized by:
a triclinic, P1 crystal system space group at a temperature of about 297 K;
unit cell dimensions a=7.7363 (10) Å, b=9.7146 (12) Å, c=9.7854 (13) Å, α=105.524 (4)°, β=110.554 (4)°, and γ=97.167 (4)°;
an XRPD having peaks at 11.5, 13.9, and 16.2°2θ±0.2° 2θ; or
an XRPD pattern substantially similar to FIG. 7.

### Claim 2

A composition comprising crystalline 4-hydroxy-N-methyltryptammonium fumarate (norpsilocin fumarate) and a second component selected from (a) a serotonergic drug, (b) a purified psilocybin derivative, (c) one or two purified cannabinoids and (d) a purified terpene,
wherein crystalline norpsilocin fumarate is characterized by:
a triclinic, P1 crystal system space group at a temperature of about 297 K;
unit cell dimensions a=7.7363 (10) Å, b=9.7146 (12) Å, c=9.7854 (13) Å, α=105.524 (4)°, β=110.554 (4)°, and γ=97.167 (4)°;
an XRPD having peaks at 11.5, 13.9, and 16.2°2θ±0.2° 2θ; or
an XRPD pattern substantially similar to FIG. 7.

### Claim 3

4-hydroxy-N-methyltryptammonium fumarate (norpsilocin fumarate).

### Claim 4 (depends on 3)

A composition comprising 4-hydroxy-N-methyltryptammonium fumarate (norpsilocin fumarate) according to claim 3 and an excipient.

### Claim 5 (depends on 3)

A composition comprising 4-hydroxy-N-methyltryptammonium fumarate (norpsilocin fumarate) according to claim 3 and a second component selected from (a) a serotonergic drug, (b) a purified psilocybin derivative, (c) one or two purified cannabinoids and (d) a purified terpene.

### Claim 6 (depends on 3)

A method of treating a psychological disorder comprising the step of:
administering to a subject in need thereof a therapeutically effective amount of 4-hydroxy-N-methyltryptammonium fumarate (norpsilocin fumarate) according to claim 3.

### Claim 7 (depends on 4)

A method of treating a psychological disorder comprising the step of:
administering to a subject in need thereof a composition according to claim 4.

### Claim 8 (depends on 3)

A method of treating inflammation and/or pain comprising the step of:
administering to a subject in need thereof a therapeutically effective amount of 4-hydroxy-N-methyltryptammonium fumarate (norpsilocin fumarate) according to claim 3.

### Claim 9 (depends on 4)

A method of treating inflammation and/or pain comprising the step of:
administering to a subject in need thereof a composition according to claim 4.

### Claim 10 (depends on 5)

A method of treating a psychological disorder comprising the step of:
administering to a subject in need thereof a composition according to claim 5.

### Claim 11 (depends on 5)

A method of treating inflammation and/or pain comprising the step of:
administering to a subject in need thereof a composition according to claim 5.