Phenylcyclopropylamine

Tranylcypromine, the simplest phenylcyclopropylamine.

Phenylcyclopropylamines, or 2-phenylcyclopropylamines, also known as phenylcypromines, are phenethylamine and amphetamine derivatives in which the alkyl side chain has been cyclized into a cyclopropyl ring. ^{[1] [2]} Examples include the monoamine oxidase inhibitor (MAOI) antidepressant tranylcypromine (trans-2-phenylcyclopropylamine) and the synthetic psychedelics DMCPA (2,5-dimethoxy-4-methylphenylcyclopropylamine) and 3,4,5-trimethoxytranylcypromine (TMT; MCPA), among various others. ^{[1] [2] [3] [4]}

References

1. Shulgin A, Manning T, Daley PF (2011). "#41. DMCPA". The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds . Vol. 1. Berkeley, CA: Transform Press. pp. 73–75. ISBN   978-0-9630096-3-0. OCLC   709667010.
2. Nichols DE, Weintraub HJ, Pfister WR, Yim GK (1978). "The Use of Rigid Analogues to Probe Hallucinogen Receptors". QuaSAR, Quantitative Structure Activity Relationships of Analgesics, Narcotic Antagonists, and Hallucinogens. Department of Health, Education, and Welfare, Public Health Service, Alcohol, Drug Abuse, and Mental Health Administration. pp. 70–83.
3. Nichols DE, Pfister WR, Yim GK (June 1978). "LSD and phenethylamine hallucinogens: new structural analogy and implications for receptor geometry". Life Sci. 22 (24): 2165–2170. doi:10.1016/0024-3205(78)90567-2. PMID   672453.
4. Usdin, Earl; Effron, Daniel H. (1972). "Aromatic Compounds: Phenethylamine Derivatives". Psychotropic Drugs and Related Compounds. National Institute of Mental Health. pp. 331–361.