Chemistry:Lophophine
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]
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.
See also
- Substituted methylenedioxyphenethylamine
- Substituted methoxyphenethylamine
- Scaline
References
- ↑ 1.00 1.01 1.02 1.03 1.04 1.05 1.06 1.07 1.08 1.09 A. Shulgin and A. Shulgin (1991). Pihkal. Berkeley: Transform Press. pp. 701–702.
- ↑ 2.0 2.1 2.2 2.3 2.4 2.5 "Psychotomimetic Agents". Psychopharmacological Agents: Use, Misuse and Abuse. Medicinal Chemistry: A Series of Monographs. 4. Academic Press. 1976. pp. 59–146. doi:10.1016/b978-0-12-290559-9.50011-9. ISBN 978-0-12-290559-9. https://bitnest.netfirms.com/external/10.1016/B978-0-12-290559-9.50011-9. "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."
- ↑ 3.0 3.1 3.2 3.3 3.4 "Лофофин (lophophine)" (in ru). https://aipsin.com/newsubstance/1518/.
- ↑ "Ecstasy analogues found in cacti". Journal of Psychoactive Drugs 40 (2): 219–22. June 2008. doi:10.1080/02791072.2008.10400635. PMID 18720674.
- ↑ "Controlled Drugs and Substances Act". https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html.
- ↑ Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026), United States: U.S. Department of Justice: Drug Enforcement Administration (DEA): Diversion Control Division, January 2026, https://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf
External links
 |  |
