3C (psychedelics)

3C (3C-x), also known as 4-substituted 3,5-dimethoxyamphetamines, substituted 3,4,5-trimethoxyamphetamine (3,4,5-TMA or TMA-1) analogues, or 3C-scalines, is a general name for the family of psychedelic amphetamines containing methoxy groups at the 3 and 5 positions of the benzene ring.^[1][2] These compounds are analogues of 3,4,5-trimethoxyamphetamine (3,4,5-TMA or TMA-1).^[1][2]

3,4,5-Trimethoxyamphetamine (3,4,5-TMA; TMA-1).

The 3C drugs are not the amphetamine counterparts of the 2C drugs, which are 4-substituted 2,5-dimethoxyphenethylamines.^[1][2] Instead, the DOx drugs, which are 4-substituted 2,5-dimethoxyamphetamines, are the amphetamine counterparts of the 2C drugs.^[1][2] The 3C drugs are the amphetamine counterparts of substituted mescaline analogues (4-substituted 3,5-dimethoxyphenethylamines).^[1][2] Moreover, in terms of naming with the "3C" prefix, the 3C drugs are generally actually derivatives of TMA-1 with the 4-position methoxy group extended rather than having any 4-position substituent.^[1][2] In this regard, they would be the 3,5-dimethoxyamphetamine counterparts of the 2C-O (2,4,5-trimethoxyphenethylamine) drugs (e.g., 2C-O-4) and the 2,4,5-trimethoxyamphetamine (2,4,5-TMA; TMA-2) derivatives (e.g., MEM).^[3][4]

3C drugs have been developed and/or studied by Alexander Shulgin^[1][2] and Daniel Trachsel,^[5][6][4][7] among others.^[8][9] The pharmacology of 3C drugs has been studied and described.^[7][8]

List of 3C drugs

4-Methoxylated

• 3,4,5-Trimethoxyamphetamine (3,4,5-TMA; TMA-1; 3C-mescaline)
• 3C-AL (3C-allylescaline) (4-allyloxy-3,5-dimethoxyamphetamine)
• 3C-BZ (3C-benzscaline) (4-benzyloxy-3,5-dimethoxyamphetamine)
• 3C-CPM (3C-cyclopropylmescaline) (4-cyclopropylmethoxy-3,5-dimethoxyamphetamine)
• 3C-DFE (3C-difluoroescaline) (4-(2,2-difluoroethoxy)-3,5-dimethoxyamphetamine)
• 3C-DFM (3C-difluoromescaline) (4-(2,2-difluoromethoxy)-3,5-dimethoxyamphetamine)
• 3C-E (3C-escaline) (4-ethoxy-3,5-dimethoxyamphetamine)
• 3C-FE (3C-fluoroescaline) (4-(2-fluoroethoxy)-3,5-dimethoxyamphetamine)
• 3C-FP (3C-fluoroproscaline) (4-(3-fluoropropoxy)-3,5-dimethoxyamphetamine)
• 3C-IB (3C-isobuscaline) (4-isobutoxy-3,5-dimethoxyamphetamine)
• 3C-IP (3C-isoproscaline) (4-isopropoxy-3,5-dimethoxyamphetamine)
• 3C-MAL (3C-methallylescaline) (4-methallyloxy-3,5-dimethoxyamphetamine)
• 3C-P (3C-proscaline) (4-propoxy-3,5-dimethoxyamphetamine)
• 3C-TFE (3C-trifluoroescaline) (4-(2,2,2-trifluoroethoxy)-3,5-dimethoxyamphetamine)

Other 4-substituted

• 4-Br-3,5-DMA (4-bromo-3,5-dimethoxyamphetamine)
• 4-I-3,5-DMA (4-iodo-3,5-dimethoxyamphetamine)
• 4-PhPr-3,5-DMA (4-(3-phenylpropyl)-3,5-dimethoxyamphetamine)

See also

• Substituted methoxyphenethylamine
• 3,5-Dimethoxyamphetamine (3,5-DMA)
• Substituted mescaline analogue
• PiHKAL (Phenethylamines I Have Known and Loved)
• The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds