MMDA-2

Last updated
MMDA-2
MMDA-2-structure.png
Clinical data
Routes of
administration 		Oral, Insufflated, Rectal
ATC code
  • none
Legal status
Legal status
Identifiers
  • 1-(6-Methoxy-1,3-benzodioxol-5-yl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C11H15NO3
Molar mass 209.245 g·mol−1
3D model (JSmol)
  • O1c2cc(c(OC)cc2OC1)CC(N)C

MMDA-2 (2-methoxy-4,5-methylenedioxyamphetamine) is a psychedelic drug of the amphetamine class. [1] It is closely related to MMDA and MDA. [1]

Alexander Shulgin was likely the first to synthesize MMDA-2. [1] In his book PiHKAL , the dose is listed as 25–50 mg, and the duration is listed as 8–12 hours. [1] Shulgin reports that MMDA-2 produces effects such as enhanced awareness, empathy, and visual facilitation and distortion, as well as some side effects like gastrointestinal upset and appetite loss. [1] He states that 30 mg is very similar to 80 mg of MDA, and also remarks that it would be impossible for anyone to have a bad experience on the drug at that dose. [1]

Scientific research has shown that MMDA-2, unlike MMDA, but similarly to 6-methyl-MDA, is only very weak at inducing the release of serotonin or dopamine, [2] and accordingly, does not produce amphetamine-like responses in animals in drug discrimination studies. [3] Instead, MMDA-2 is likely to act as a pure 5-HT2 receptor agonist similarly to the DOx series of compounds, with activation of the 5-HT2A receptor conferring its psychedelic effects. [4]

MMDA-2 has been sold as a designer drug in Japan. [5]

Related Research Articles

2C-B Chemical compound

2C-B (4-Bromo-2,5-dimethoxyphenethylamine) is a psychedelic drug of the 2C family. It was first synthesized by Alexander Shulgin in 1974. In Shulgin's book PiHKAL, the dosage range is listed as 12–24 mg. As a recreational drug, 2C-B is sold as a white powder sometimes pressed in tablets or gel caps. It is also referred to by a number of street names. The drug is usually taken orally, but can also be insufflated or vaporized. While being primarily a psychedelic it is also a mild entactogen.

2,5-Dimethoxy-4-methylamphetamine Chemical compound

2,5-Dimethoxy-4-methylamphetamine is a psychedelic and a substituted amphetamine. It was first synthesized by Alexander Shulgin, and later reported in his book PiHKAL: A Chemical Love Story. DOM is classified as a Schedule I substance in the United States, and is similarly controlled in other parts of the world. Internationally, it is a Schedule I drug under the Convention on Psychotropic Substances. It is generally taken orally.

2,5-Dimethoxy-4-bromoamphetamine Chemical compound

Dimethoxybromoamphetamine (DOB), also known as brolamfetamine (INN) and bromo-DMA, is a psychedelic drug and substituted amphetamine of the phenethylamine class of compounds. DOB was first synthesized by Alexander Shulgin in 1967. Its synthesis and effects are documented in Shulgin's book PiHKAL: A Chemical Love Story.

3,4-Methylenedioxyamphetamine Empathogen-entactogen, psychostimulant, and psychedelic drug of the amphetamine family

3,4-Methylenedioxyamphetamine is an empathogen-entactogen, psychostimulant, and psychedelic drug of the amphetamine family that is encountered mainly as a recreational drug. In terms of pharmacology, MDA acts most importantly as a serotonin–norepinephrine–dopamine releasing agent (SNDRA). In most countries, the drug is a controlled substance and its possession and sale are illegal.

2,5-Dimethoxy-4-ethylamphetamine Chemical compound

2,5-Dimethoxy-4-ethylamphetamine is a psychedelic drug of the phenethylamine and amphetamine chemical classes. It was first synthesized by Alexander Shulgin, and was described in his book PiHKAL.

MMDA (drug) Entactogen drug

MMDA is a psychedelic and entactogen drug of the amphetamine class. It is an analogue of lophophine, MDA, and MDMA.

EDMA Chemical compound

3,4-Ethylenedioxy-N-methylamphetamine (EDMA) is an entactogen drug of the methamphetamine class. It is an analogue of MDMA where the methylenedioxy ring has been replaced by an ethylenedioxy ring. EDMA was first synthesized by Alexander Shulgin. In his book PiHKAL, the dosage is listed as 150–250 mg, and the duration listed as 3–5 hours. According to Shulgin, EDMA produces a bare threshold consisting of paresthesia, nystagmus, and hypnogogic imagery, with few to no other effects. Scientific research has demonstrated that EDMA acts as a non-neurotoxic serotonin releasing agent with moderately diminished potency relative to MDMA, and with negligible effects on dopamine release.

Ariadne (psychedelic) Chemical compound

Ariadne is a lesser-known psychedelic drug. It is a homologue of 2C-D and DOM. Ariadne was first synthesized by Alexander Shulgin. In his book PiHKAL, Shulgin reported testing Ariadne up to a dose of 32 mg, and reported that it produces psychedelia at a bare threshold. Very little data exists about the pharmacological properties, metabolism, and toxicity of Ariadne in humans apart from Shulgin's limited testing.

2-Bromo-4,5-methylenedioxyamphetamine Chemical compound

2-Bromo-4,5-methylenedioxyamphetamine (6-Bromo-MDA) is a lesser-known psychedelic drug and a substituted amphetamine. It was first synthesized by Alexander Shulgin. In his book PiHKAL, the dose is listed as 350 mg and the duration unknown. It produces stimulant effects but with no psychedelic or empathogenic action. Very little data exists about its pharmacological properties, metabolism, and toxicity.

DMMDA Psychedelic drug

2,5-Dimethoxy-3,4-methylenedioxyamphetamine (DMMDA) is a psychedelic drug of the phenethylamine and amphetamine chemical classes. It was first synthesized by Alexander Shulgin and was described in his book PiHKAL. Shulgin listed the dosage as 30–75 mg and the duration as 6–8 hours. He reported DMMDA as producing LSD-like images, mydriasis, ataxia, and time dilation.

1,3-Benzodioxolylbutanamine Chemical compound

1,3-Benzodioxolylbutanamine is an entactogenic drug of the phenethylamine chemical class. It is the α-ethyl analog of MDPEA and MDA and the methylenedioxy analogue of α-ethylphenethylamine.

2,5-Dimethoxy-4-ethoxyamphetamine Psychedelic drug

2,5-Dimethoxy-4-ethoxyamphetamine (MEM) is a psychedelic drug of the phenethylamine and amphetamine chemical classes. It was first synthesized by Alexander Shulgin. In his book PiHKAL, he lists the active dose range as 20–50 mg, and the duration as 10–14 hours. According to Shulgin, MEM produces color enhancement, visual phenomena, and pattern movement, among other effects.

3,4-Methylenedioxy-<i>N</i>-isopropylamphetamine Chemical compound

3,4-Methylenedioxy-N-isopropylamphetamine is a psychoactive drug of the phenethylamine and amphetamine chemical classes which acts as an entactogen, psychedelic, and stimulant. It is the N-isopropyl analogue of 3,4-methylenedioxyamphetamine (MDA). MDIP was first synthesized by Alexander Shulgin. In his book PiHKAL, the minimum dosage is listed as 250 mg. MDIP produces a mild threshold. Very little is known about the pharmacology, pharmacokinetics, effects, and toxicity of MDIP.

Naphthylaminopropane Chemical compound

Naphthylaminopropane (PAL-287) is an experimental drug under investigation as of 2007 for the treatment of alcohol and stimulant addiction.

Methyl-MMDA-2

N-Methyl-2-methoxy-4,5-methylenedioxyamphetamine is a psychedelic drug of the amphetamine class. It is the N-methylated derivative of MMDA-2, and it is also an analog of MDMA and 6-methyl-MDA.

5-Methyl-MDA

5-Methyl-3,4-methylenedioxyamphetamine (5-Methyl-MDA) is an entactogen and psychedelic designer drug of the amphetamine class. It is a ring-methylated homologue of MDA and a structural isomer of MDMA.

MDAI Chemical compound

MDAI (5,6-methylenedioxy-2-aminoindane) is a drug developed in the 1990s by a team led by David E. Nichols at Purdue University. It acts as a non-neurotoxic and highly selective serotonin releasing agent (SSRA) in vitro and produces entactogen effects in humans.

A serotonin releasing agent (SRA) is a type of drug that induces the release of serotonin into the neuronal synaptic cleft. A selective serotonin releasing agent (SSRA) is an SRA with less significant or no efficacy in producing neurotransmitter efflux at other types of monoamine neurons.

2,5-Dimethoxy-4-fluoroamphetamine Chemical compound

2,5-Dimethoxy-4-fluoroamphetamine (DOF) is a psychedelic drug of the phenethylamine and amphetamine classes. Alexander Shulgin briefly describes DOF in his book PiHKAL:

Animal studies that have compared DOF to the highly potent DOI and DOB imply that the human activity will be some four to six times less than these two heavier halide analogues.

3,4-Ethylidenedioxyamphetamine Chemical compound

3,4-Ethylidenedioxyamphetamine (EIDA) is a substituted derivative of 3,4-methylenedioxyamphetamine (MDA), which was developed by David Nichols and coworkers, in the course of research to determine the bulk tolerance around the benzodioxole portion of the MDA molecule. EIDA was found to produce similar effects to MDA in animals but with less than half the potency, while the isopropylidenedioxy derivative did not substitute for MDA and instead had sedative and convulsant effects. This shows limited bulk tolerance at this position and makes it likely the activity of EIDA will reside primarily in one enantiomer, although only the racemic mix has been studied as yet.

References

  1. 1 2 3 4 5 6 Ann Shulgin; Alexander Shulgin (1991). Pihkal: A Chemical Love Story. Transform Press. ISBN   978-0-9630096-0-9.
  2. ↑ McKenna DJ, Guan XM, Shulgin AT (March 1991). "3,4-Methylenedioxyamphetamine (MDA) analogues exhibit differential effects on synaptosomal release of 3H-dopamine and 3H-5-hydroxytryptamine". Pharmacology Biochemistry and Behavior. 38 (3): 505–12. doi:10.1016/0091-3057(91)90005-M. PMID   1829838. S2CID   2740262.
  3. ↑ Glennon RA, Yousif M, Naiman N, Kalix P (March 1987). "Methcathinone: a new and potent amphetamine-like agent". Pharmacology Biochemistry and Behavior. 26 (3): 547–51. doi:10.1016/0091-3057(87)90164-X. PMID   3575369. S2CID   5890314.
  4. ↑ Clare BW (2002). "QSAR of benzene derivatives: comparison of classical descriptors, quantum theoretic parameters and flip regression, exemplified by phenylalkylamine hallucinogens" (PDF). Journal of Computer-aided Molecular Design. 16 (8–9): 611–33. Bibcode:2002JCAMD..16..611C. doi:10.1023/A:1021966231380. PMID   12602954. S2CID   9948738.
  5. ↑ Min JZ, Shimizu Y, Toyo'oka T, Inagaki S, Kikura-Hanajiri R, Goda Y (October 2008). "Simultaneous determination of 11 designated hallucinogenic phenethylamines by ultra-fast liquid chromatography with fluorescence detection". Journal of Chromatography B. 873 (2): 187–94. doi:10.1016/j.jchromb.2008.08.020. PMID   18789774.
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