Deuterium free, stable isotope labeled 2-phenylethylamine hallucinogens and/or stimulants, methods of their preparation and their use

A method of preparing a deuterium free, stable isotope labeled hallucinogen and/or stimulant containing a 2-phenylethylamine-based structural unit of general formula I:

• wherein:
• R1, R2 independently of each other, represent hydrogen atom or an organic residue selected from
• organic residues consisting of saturated or unsaturated substituted or unsubstituted alkyl, cycloalkyl, aryl, alkylcycloalkyl, alkylaryl, cycloalkylaryl or alkylcycloalkylaryl groups containing or not containing at least one heteroatom;
• and
• organic residues containing at least two different groups selected from saturated and unsaturated, substituted and unsubstituted alkyl, cycloalkyl, aryl, alkylcycloalkyl, alkylaryl, cycloalkylaryl and alkylcycloalkylaryl groups containing or not containing at least one heteroatom;
• R3 and R4 taken together represent a carbonyl oxygen atom or a substituted or unsubstituted imino group or independently of each other have the meanings given below for R7 to R11;
• R5 and R6 taken together represent a carbonyl oxygen atom or substituted or unsubstituted imino group or independently of each other have the meanings given below for R7 to R11;
• R7 to R11 independently of each other represent a hydrogen atom, a hydroxy group, an amino group, a mercapto group, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a nitrile group or an organic residue selected from
• organic residues consisting of saturated or unsaturated substituted or unsubstituted alkyl, cycloalkyl, aryl, alkylcycloalkyl, alkylaryl, cycloalkylaryl or alkylcycloalkylaryl groups containing or not containing at least one heteroatom;
• and
• organic residues containing at least two different groups selected from saturated and unsaturated, substituted and unsubstituted alkyl, cycloalkyl, aryl, alkylcycloalkyl, alkylaryl, cycloalkylaryl and alkylcycloalkylaryl groups containing or not containing at least one heteroatom;
• wherein the method comprises
• (1) reacting [13C6]-benzaldehyde or a substituted [13C6]-benzaldehyde with a nitro group containing compound of general formula II:
• O2N—CH2—R3 (II),
• to obtain a substituted or unsubstituted nitro compound of general formula III as an intermediate:
• wherein R3, R7, R8, R9, R10 and R11 have the meanings set forth above;
• and
• (2) reducing the NO2 group and hydrogenating the olefinic double bond of the intermediate of general formula III to obtain a 2-phenylethylamine alkaloid or a psychotropic drug of general formula I, wherein R1, R2, R4, R5 and R6 are hydrogen atoms.