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MMDA-3b


FieldValue
imageMMDA-3b.svg
image_classskin-invert-image
routes_of_administrationOral
classSerotonergic psychedelic; Hallucinogen; Serotonin releasing agent
ATC_prefixNone
onsetUnknown
duration_of_actionUnknown
CAS_number23693-20-1
PubChem44374894
ChemSpiderID23231727
UNIIFM6SU6FD7Y
ChEMBL159299
synonyms4-MeO-2,3-MDA; 4-Methoxy-2,3-methylenedioxyamphetamine; 2,3-Methylenedioxy-4-methoxyamphetamine; 4-Methoxy-ORTHO-MDA; 4-MeO-ORTHO-MDA
IUPAC_name1-(7-methoxy-1,3-benzodioxol-4-yl)propan-2-amine
C11H=15N=1O=3
SMILESCC(CC1=C2C(=C(C=C1)OC)OCO2)N
StdInChI1S/C11H15NO3/c1-7(12)5-8-3-4-9(13-2)11-10(8)14-6-15-11/h3-4,7H,5-6,12H2,1-2H3
StdInChIKeyCLRZDDLQTLKYFH-UHFFFAOYSA-N

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MMDA-3b, also known as 4-methoxy-2,3-methylenedioxyamphetamine (4-MeO-2,3-MDA), is a psychedelic drug of the phenethylamine, amphetamine, and MDxx families related to ORTHO-MDA (2,3-MDA). It is the 4-methoxy derivative of ORTHO-MDA and is a positional isomer of MMDA (5-MeO-3,4-MDA) and related compounds like MMDA-2 (6-MeO-3,4-MDA) and MMDA-3a (2-MeO-3,4-MDA).

MMDA-3b was included as an entry in Alexander Shulgin's book PiHKAL (Phenethylamines I Have Known and Loved). He lists its dose as greater than 80mg orally and its duration as unknown. Shulgin describes 60mg as being definitely active, qualitatively like 3,4-methylenedioxyamphetamine (MDA), but quantitatively perhaps less, whereas an 80mg dose of MMDA-3b was said to be no more effective than the 60mg dose. He also says that it is similar at these doses to 20mg MMDA-3a and may be about 3-fold less potent than MMDA-3a. Elsewhere, MMDA-3b is described as 3-fold more potent than mescaline. Little is known about the drug. The chemical synthesis of MMDA-3b was also described in PiHKAL.

MMDA-3b has been found to act as an efficacious serotonin releasing agent with little effect on dopamine similarly to MMDA. For comparison, MDA and MDMA release both serotonin and dopamine, whereas MMDA-2 releases neither serotonin nor dopamine.

MMDA-3b was first described in the scientific literature by Shulgin in 1964. It was subsequently described in greater detail by Shulgin in his book PiHKAL in 1991. Other 2,3-MDA positional isomers of MMDA-3b include MMDA-4 and MMDA-5.

MMDA-3b is a controlled substance in Canada under phenethylamine blanket-ban language.

References

References

  1. Shulgin, Alexander T.. (1978). "Stimulants". Springer US.
  2. {{CitePiHKAL https://erowid.org/library/books_online/pihkal/pihkal135.shtml
  3. (1994). "Hallucinogens: An Update". National Institute on Drug Abuse.
  4. (1975). "Hallucinogenic Agents". Wright-Scientechnica.
  5. (March 1991). "3,4-Methylenedioxyamphetamine (MDA) analogues exhibit differential effects on synaptosomal release of 3H-dopamine and 3H-5-hydroxytryptamine". Pharmacol Biochem Behav.
  6. (July 1964). "Psychotomimetic amphetamines: methoxy 3,4-dialkoxyamphetamines". Experientia.
  7. "Controlled Drugs and Substances Act".
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