Lophophine (original) (raw)
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Chemical compound
Pharmaceutical compound
Lophophine
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| Clinical data | |
| Other names | 3-Methoxy-4,5-methylenedioxyphenethylamine; MMDPEA |
| Routes of administration | Oral |
| ATC code | none |
| Legal status | |
| Legal status | Uncontrolled (but may be covered under the Federal Analogue Act in the United States and under similar bills in other countries due to its similarity to mescaline and MMDA) |
| Identifiers | |
| IUPAC name 2-(7-methoxy-1,3-benzodioxol-5-yl)ethanamine | |
| CAS Number | 23693-38-1  Y |
| PubChem CID | 90239 |
| ChemSpider | 81465 Y |
| UNII | C68IB79RC2 |
| ChEMBL | ChEMBL159620 Y |
| CompTox Dashboard (EPA) | DTXSID80178357  |
| ECHA InfoCard | 100.041.645 |
| Chemical and physical data | |
| Formula | C10H13NO3 |
| Molar mass | 195.218 g·mol−1 |
| 3D model (JSmol) | Interactive image |
| SMILES O1c2cc(cc(OC)c2OC1)CCN | |
| InChI InChI=1S/C10H13NO3/c1-12-8-4-7(2-3-11)5-9-10(8)14-6-13-9/h4-5H,2-3,6,11H2,1H3 YKey:ORXQUAPZHKCCAX-UHFFFAOYSA-N Y |
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Lophophine, also known as 3-methoxy-4,5-methylenedioxyphenethylamine (MMDPEA), is a putative psychedelic and entactogen drug of the methylenedioxyphenethylamine family. It is the α-demethylated homologue of MMDA, and is also closely related to mescaline.
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.[2]
Shulgin reports that lophophine is active in the dosage range of 150–250 mg. 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. Shulgin also notes that (in contrast to mescaline), lophophine causes no nausea.[1]
- Substituted methylenedioxyphenethylamine
- Substituted methoxyphenethylamine
- Substituted mescaline analogue
- 3,4-Methylenedioxyphenethylamine (MDPEA)
- ^ a b A. Shulgin and A. Shulgin (1991). Pihkal. Berkeley: Transform Press. pp. 701–702.
- ^ Bruhn JG, El-Seedi HR, Stephanson N, Beck O, Shulgin AT (June 2008). "Ecstasy analogues found in cacti". Journal of Psychoactive Drugs. 40 (2): 219–22. CiteSeerX 10.1.1.689.4014. doi:10.1080/02791072.2008.10400635. PMID 18720674. S2CID 11251286.