Lophophine
Chemical compound
From Wikipedia, the free encyclopedia
Lophophine, also known as 2C-MMDA-1, 5-methoxy-MDPEA, or 3-methoxy-4,5-methylenedioxyphenethylamine (MMDPEA or MMDPEA-1), is a psychedelic drug of the methylenedioxyphenethylamine family.[1][2][3] It is the α-demethylated homologue of MMDA, and is also closely related to mescaline (3,4,5-trimethoxyphenethylamine) and MDPEA.[1][2] Lophophine has been encountered as a novel designer drug.[3]
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| Other names | 2C-MMDA; 2C-MMDA-1; MMDPEA; MMDPEA-1; 3-Methoxy-4,5-methylenedioxyphenethylamine; 5-Methoxy-MDPEA |
| Routes of administration | Oral[1][2] |
| Drug class | Serotonergic psychedelic; Hallucinogen |
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| ECHA InfoCard | 100.041.645 |
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| Formula | C10H13NO3 |
| Molar mass | 195.218 g·mol−1 |
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Use and effects
Alexander Shulgin reported in PiHKAL (Phenethylamines I Have Known and Loved) and other publications that lophophine is active in the dose range of 150 to 250 mg orally.[1][2][3] He states that at these doses, lophophine has some similarity to mescaline in action, in producing a peaceful elevation of mood, euphoria, and mild enhancement of visual perception, but without the generation of closed-eye mental imagery.[1][2] Shulgin also notes that, in contrast to mescaline, lophophine causes no nausea.[1][2] He estimated that it was about twice the potency of mescaline.[1][2]
Interactions
Chemistry
Lophophine, also known as 3-methoxy-4,5-methylenedioxyphenethylamine, is a phenethylamine and methylenedioxyphenethylamine (MDxx) derivative.[1][3]
Synthesis
The chemical synthesis of lophophine has been described.[1]
Analogues
Analogues of lophophine (5-methoxy-MDPEA or 2C-MMDA-1) include mescaline (3,4,5-trimethoxyphenethylamine), 3,4-methylenedioxyphenethylamine (MDPEA), 2C-MMDA-2 (MMDPEA-2), 2C-MMDA-3a (MMDPEA-3a), and MMDA (5-methoxy-MDA), among others.[1]
Natural occurrence
Alexander Shulgin originally suggested that lophophine may be a natural constituent of peyote (Lophophora williamsii) due to it being the only logical chemical intermediate for the biosynthesis of several tetrahydroisoquinolines known to be present in this cactus species.[1] Subsequently, lophophine was indeed shown to be a minor component of both peyote and San Pedro cactus.[4]
History
Lophophine was encountered as a novel designer drug in Europe in 2023.[3]
Society and culture
Legal status
Canada
Lophophine is controlled substance in Canada under phenethylamine blanket-ban language.[5]
United States
Lophophine is not an explicitly controlled substance in the United States.[6] However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.