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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 |
| Chemical and physical data | |
| Formula | C10H13NO3 |
| Molar mass | 195.218 g·mol−1 |
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Lophophine, also known as2C-MMDA-1,5-methoxy-MDPEA, or3-methoxy-4,5-methylenedioxyphenethylamine (MMDPEA orMMDPEA-1), is apsychedelicdrug of themethylenedioxyphenethylamine family.[1][2][3] It is theα-demethylatedhomologue ofMMDA, and is also closely related tomescaline (3,4,5-trimethoxyphenethylamine) andMDPEA.[1][2] Lophophine has been encountered as a noveldesigner drug.[3]
Alexander Shulgin reported in his publications that lophophine is active in thedose range of 150 to 250 mgorally.[1][2][3] He states that at these doses, lophophine has some similarity to mescaline in action, in producing a peaceful elevation ofmood,euphoria, and mild enhancement ofvisualperception, but without the generation ofclosed-eyemental imagery.[1][2] Shulgin also notes that, in contrast to mescaline, lophophine causes nonausea.[1][2] He estimated that it was about twice thepotency of mescaline.[1][2]
Lophophine, also known as 3-methoxy-4,5-methylenedioxyphenethylamine, is aphenethylamine andmethylenedioxyphenethylamine (MDxx)derivative.[1][3]
Thechemical synthesis of lophophine has been described.[1]
Analogues of lophophine (5-methoxy-MDPEA or 2C-MMDA-1) includemescaline (3,4,5-trimethoxyphenethylamine),3,4-methylenedioxyphenethylamine (MDPEA),2C-MMDA-2 (MMDPEA-2),2C-MMDA-3a (MMDPEA-3a), andMMDA (5-methoxy-MDA), among others.[1]
Alexander Shulgin originally suggested that lophophine may be anatural constituent ofpeyote (Lophophora williamsii) due to it being the only logicalchemical intermediate for thebiosynthesis of severaltetrahydroisoquinolines known to be present in this cactus species.[1] Subsequently, lophophine was indeed shown to be a minor component of both peyote andSan Pedro cactus.[4]
Lophophine was encountered as a noveldesigner drug inEurope in 2023.[3]
Lophophine iscontrolled substance inCanada under phenethylamine blanket-ban language.[5]
Lophophine is not an explicitlycontrolled substance in theUnited States.[6] However, it could be considered acontrolled substance under theFederal Analogue Act if intended for human consumption.
Another compound is homomyristicylamine [lophophine (LIX)], which also has never been observed in the peyote plant, but which presents an obvious theoretical potential as a biosynthetic precursor of the tetrahydroisoquinoline alkaloids such as lophophorine and anhalonine (Kapatia et al., 1969). This compound is active in man at dosage levels of 150-200 mg, about twice the potency of mescaline (A. T. Shulgin, unpublished data, 1973). The qualitative description of its action is quite similar to that of mescaline in that there is a peaceful elevation of mood, the generation of an euphoric state, and the enhancement of visual perception, especially in the color sense. There are dissimilarities, particularly in that there is little if any nausea and there is no visual distortion. These latter differences disappear at dosages of 300 mg, and there is the generation of eyes-closed imagery similar to that observed with mescaline.
