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Lophophine information


Lophophine
Clinical data
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 checkY
PubChem CID
  • 90239
ChemSpider
  • 81465 checkY
UNII
  • C68IB79RC2
ChEMBL
  • ChEMBL159620 checkY
CompTox Dashboard (EPA)
  • DTXSID80178357 Edit this at Wikidata
ECHA InfoCard100.041.645 Edit this at Wikidata
Chemical and physical data
FormulaC10H13NO3
Molar mass195.218 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 checkY
  • Key:ORXQUAPZHKCCAX-UHFFFAOYSA-N checkY
  (verify)

Lophophine (MMDPEA or 3-methoxy-4,5-methylenedioxyphenethylamine) is a putative psychedelic and entactogen drug of the methylenedioxyphenethylamine class. 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]

  1. ^ a b A. Shulgin and A. Shulgin (1991). Pihkal. Berkeley: Transform Press. pp. 701–702.
  2. ^ 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.

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Lophophine

Last Update:

Lophophine (MMDPEA or 3-methoxy-4,5-methylenedioxyphenethylamine) is a putative psychedelic and entactogen drug of the methylenedioxyphenethylamine class...

Word Count : 230

Cocaine

Last Update:

Isoetarine Isoprenaline L-Deprenyl (Selegiline) Lefetamine Lisdexamfetamine Lophophine MBDB MDA (tenamfetamine) MDBU MDEA MDMA (midomafetamine) MDMPEA MDOH MDPR...

Word Count : 17671

MDMA

Last Update:

DOiPR DOM DON DOPR DOTFM MEM HOT-x HOT-2 HOT-7 HOT-17 MDxx DMMDA DMMDA-2 Lophophine MDA MDAI MDBZ MDMA MMDA MMDA-2 MMDA-3a MMDMA Mescaline (subst.) 2-Bromomescaline...

Word Count : 15751

List of naturally occurring phenethylamines

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including monoamine oxidases. Substituted phenethylamines like mescaline and lophophine are found in psychoactive cactus. T. A. Smith (1977) Phytochemistry 16...

Word Count : 62

Methamphetamine

Last Update:

Isoetarine Isoprenaline L-Deprenyl (Selegiline) Lefetamine Lisdexamfetamine Lophophine MBDB MDA (tenamfetamine) MDBU MDEA MDMA (midomafetamine) MDMPEA MDOH MDPR...

Word Count : 14825

LSD

Last Update:

DOiPR DOM DON DOPR DOTFM MEM HOT-x HOT-2 HOT-7 HOT-17 MDxx DMMDA DMMDA-2 Lophophine MDA MDAI MDBZ MDMA MMDA MMDA-2 MMDA-3a MMDMA Mescaline (subst.) 2-Bromomescaline...

Word Count : 16533

Ketamine

Last Update:

DOiPR DOM DON DOPR DOTFM MEM HOT-x HOT-2 HOT-7 HOT-17 MDxx DMMDA DMMDA-2 Lophophine MDA MDAI MDBZ MDMA MMDA MMDA-2 MMDA-3a MMDMA Mescaline (subst.) 2-Bromomescaline...

Word Count : 11355

Adderall

Last Update:

Isoetarine Isoprenaline L-Deprenyl (Selegiline) Lefetamine Lisdexamfetamine Lophophine MBDB MDA (tenamfetamine) MDBU MDEA MDMA (midomafetamine) MDMPEA MDOH MDPR...

Word Count : 19815

Amphetamine

Last Update:

Furfenorex Hordenine 4-Hydroxyamphetamine Iofetamine (123I) Lisdexamfetamine Lophophine Mefenorex Mephedrone Metamfepramone Methamphetamine Dextromethamphetamine...

Word Count : 25315

Ayahuasca

Last Update:

DOiPR DOM DON DOPR DOTFM MEM HOT-x HOT-2 HOT-7 HOT-17 MDxx DMMDA DMMDA-2 Lophophine MDA MDAI MDBZ MDMA MMDA MMDA-2 MMDA-3a MMDMA Mescaline (subst.) 2-Bromomescaline...

Word Count : 10857

Aromatic compound

Last Update:

DOiPR DOM DON DOPR DOTFM MEM HOT-x HOT-2 HOT-7 HOT-17 MDxx DMMDA DMMDA-2 Lophophine MDA MDAI MDBZ MDMA MMDA MMDA-2 MMDA-3a MMDMA Mescaline (subst.) 2-Bromomescaline...

Word Count : 2113

Promethazine

Last Update:

PHA-57378 PNU-22394 PNU-181731 RH-34 SCHEMBL5334361 Phenethylamines (e.g., lophophine, mescaline) Piperazines (e.g., BZP, quipazine, TFMPP) Serotonin (5-HT)...

Word Count : 2670

Ephedrine

Last Update:

Furfenorex Hordenine 4-Hydroxyamphetamine Iofetamine (123I) Lisdexamfetamine Lophophine Mefenorex Mephedrone Metamfepramone Methamphetamine Dextromethamphetamine...

Word Count : 4412

Cannabidiol

Last Update:

PHA-57378 PNU-22394 PNU-181731 RH-34 SCHEMBL5334361 Phenethylamines (e.g., lophophine, mescaline) Piperazines (e.g., BZP, quipazine, TFMPP) Serotonin (5-HT)...

Word Count : 11097

Psilocybin

Last Update:

DOiPR DOM DON DOPR DOTFM MEM HOT-x HOT-2 HOT-7 HOT-17 MDxx DMMDA DMMDA-2 Lophophine MDA MDAI MDBZ MDMA MMDA MMDA-2 MMDA-3a MMDMA Mescaline (subst.) 2-Bromomescaline...

Word Count : 14661

Aripiprazole

Last Update:

PHA-57378 PNU-22394 PNU-181731 RH-34 SCHEMBL5334361 Phenethylamines (e.g., lophophine, mescaline) Piperazines (e.g., BZP, quipazine, TFMPP) Serotonin (5-HT)...

Word Count : 9149

Methylphenidate

Last Update:

Isoetarine Isoprenaline L-Deprenyl (Selegiline) Lefetamine Lisdexamfetamine Lophophine MBDB MDA (tenamfetamine) MDBU MDEA MDMA (midomafetamine) MDMPEA MDOH MDPR...

Word Count : 12246

Chloroform

Last Update:

DOiPR DOM DON DOPR DOTFM MEM HOT-x HOT-2 HOT-7 HOT-17 MDxx DMMDA DMMDA-2 Lophophine MDA MDAI MDBZ MDMA MMDA MMDA-2 MMDA-3a MMDMA Mescaline (subst.) 2-Bromomescaline...

Word Count : 5618

Phentermine

Last Update:

Furfenorex Hordenine 4-Hydroxyamphetamine Iofetamine (123I) Lisdexamfetamine Lophophine Mefenorex Mephedrone Metamfepramone Methamphetamine Dextromethamphetamine...

Word Count : 1710

Cyclobenzaprine

Last Update:

PHA-57378 PNU-22394 PNU-181731 RH-34 SCHEMBL5334361 Phenethylamines (e.g., lophophine, mescaline) Piperazines (e.g., BZP, quipazine, TFMPP) Serotonin (5-HT)...

Word Count : 1690

Doxylamine

Last Update:

DOiPR DOM DON DOPR DOTFM MEM HOT-x HOT-2 HOT-7 HOT-17 MDxx DMMDA DMMDA-2 Lophophine MDA MDAI MDBZ MDMA MMDA MMDA-2 MMDA-3a MMDMA Mescaline (subst.) 2-Bromomescaline...

Word Count : 3073

List of psychedelic drugs

Last Update:

active constituent of certain cacti, such as peyote and San Pedro cactus Lophophine†, also known as 'MMDPEA'; another active constituent of certain cacti...

Word Count : 3881

Toluene

Last Update:

DOiPR DOM DON DOPR DOTFM MEM HOT-x HOT-2 HOT-7 HOT-17 MDxx DMMDA DMMDA-2 Lophophine MDA MDAI MDBZ MDMA MMDA MMDA-2 MMDA-3a MMDMA Mescaline (subst.) 2-Bromomescaline...

Word Count : 3064

Quetiapine

Last Update:

PHA-57378 PNU-22394 PNU-181731 RH-34 SCHEMBL5334361 Phenethylamines (e.g., lophophine, mescaline) Piperazines (e.g., BZP, quipazine, TFMPP) Serotonin (5-HT)...

Word Count : 6534

Serotonin

Last Update:

PHA-57378 PNU-22394 PNU-181731 RH-34 SCHEMBL5334361 Phenethylamines (e.g., lophophine, mescaline) Piperazines (e.g., BZP, quipazine, TFMPP) Serotonin (5-HT)...

Word Count : 13724

Hydroxyzine

Last Update:

PHA-57378 PNU-22394 PNU-181731 RH-34 SCHEMBL5334361 Phenethylamines (e.g., lophophine, mescaline) Piperazines (e.g., BZP, quipazine, TFMPP) Serotonin (5-HT)...

Word Count : 3708

Diphenhydramine

Last Update:

DOiPR DOM DON DOPR DOTFM MEM HOT-x HOT-2 HOT-7 HOT-17 MDxx DMMDA DMMDA-2 Lophophine MDA MDAI MDBZ MDMA MMDA MMDA-2 MMDA-3a MMDMA Mescaline (subst.) 2-Bromomescaline...

Word Count : 6172

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