Dimethoxyamphetamine

Last updated

Dimethoxyamphetamine (DMA) is a series of six lesser-known psychedelic drugs similar in structure to the three isomers of methoxyamphetamine and six isomers of trimethoxyamphetamine. The isomers are 2,3-DMA, 2,4-DMA, 2,5-DMA, 2,6-DMA, 3,4-DMA, and 3,5-DMA. Three of the isomers were characterized by Alexander Shulgin in his book PiHKAL . [1] Little is known about their dangers or toxicity.

Contents

Positional isomers

2,4-DMA

2,4-Dimethoxyamphetamine
2,4-DMA.png
Names
IUPAC name
1-(2,4-dimethoxyphenyl)propan-2-amine
Identifiers
Abbreviations2,4-DMA
ChEMBL
ChemSpider
PubChem CID
UNII
  • InChI=1S/C11H17NO2/c1-8(12)6-9-4-5-10(13-2)7-11(9)14-3/h4-5,7-8H,6,12H2,1-3H3
    Key: DQWOZMUBHQPFFF-UHFFFAOYSA-N
Properties
C11H17NO2
Molar mass 195.262 g·mol−1
Pharmacology
Legal status
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

2,5-DMA

2,5-Dimethoxyamphetamine
2,5-DMA.svg
Names
IUPAC name
1-(2,5-dimethoxyphenyl)propan-2-amine
Identifiers
Abbreviations2,5-DMA
ChEMBL
ChemSpider
EC Number
  • 220-540-2
PubChem CID
UNII
  • InChI=1S/C11H17NO2/c1-8(12)6-9-7-10(13-2)4-5-11(9)14-3/h4-5,7-8H,6,12H2,1-3H3
    Key: LATVFYDIBMDBSY-UHFFFAOYSA-N
Properties
C11H17NO2
Molar mass 195.262 g·mol−1
Pharmacology
Legal status
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

2,5-DMA is the alpha-methyl homologue of 2C-H and could be called "DOH" under the DO naming scheme.

3,4-DMA

3,4-Dimethoxyamphetamine
3,4-dma.png
Names
IUPAC name
1-(3,4-dimethoxyphenyl)propan-2-amine
Identifiers
Abbreviations3,4-DMA
ChEMBL
ChemSpider
EC Number
  • 204-383-7
PubChem CID
UNII
  • InChI=1S/C11H17NO2/c1-8(12)6-9-4-5-10(13-2)11(7-9)14-3/h4-5,7-8H,6,12H2,1-3H3
    Key: KAZPHAGSWZTKDW-UHFFFAOYSA-N
Properties
C11H17NO2
Molar mass 195.262 g·mol−1
Pharmacology
Legal status
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Note that two other positional isomers of dimethoxyamphetamine, 2,6-DMA and 3,5-DMA, have also been made, but these drugs have not been tested in humans and their effects are unknown. However, it is likely that these compounds would also produce amphetamine-like stimulation or possibly hallucinogenic effects.

United States

2,5-Dimethoxyamphetamine is listed as a Scheduled I controlled substance at the federal level in the United States and is therefore illegal to buy, possess, and sell. [4] 2,4-dimethoxyamphetamine, 2,6-dimethoxyamphetamine, 3,4-dimethoxyamphetamine, and 3,5-dimethoxyamphetamine are each position isomers of 2,5-dimethoxyamphetamine, they are therefore all Schedule I controlled substances as well.

Australia

DMA is considered a Schedule 9 prohibited substance in Australia under the Poisons Standard (October 2015). [5] A Schedule 9 substance is a substance which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of Commonwealth and/or State or Territory Health Authorities. [5]

New Zealand

DMA is considered a Class A controlled drug under the Misuse of Drugs Act 1975. [6]

See also

Related Research Articles

<i>PiHKAL</i> 1991 book by Alexander Shulgin and Ann Shulgin

PiHKAL: A Chemical Love Story is a book by Dr. Alexander Shulgin and Ann Shulgin, published in 1991. The subject of the work is psychoactive phenethylamine chemical derivatives, notably those that act as psychedelics and/or empathogen-entactogens. The main title, PiHKAL, is an acronym that stands for "Phenethylamines I Have Known and Loved."

<span class="mw-page-title-main">Escaline</span> Chemical compound

Escaline (3,5-methoxy-4-ethoxyphenethylamine) is a psychedelic drug and entheogen of the phenethylamine class of compounds. Escaline was first synthesized and reported in the scientific literature by Benington, et al., in 1954, but was later re-examined in the laboratory of David E. Nichols, who prepared a series of mescaline analogues that included escaline, proscaline, and isoproscaline. The effects of this and related mescaline analogues in humans were first described by Alexander Shulgin. In his book PiHKAL , Shulgin lists the dosage range as 40 to 60 mg, consumed orally. The duration of action was stated to be 8–12 hours.

<span class="mw-page-title-main">2C-T-4</span> Chemical compound

2C-T-4 (2,5-dimethoxy-4-isopropylthiophenethylamine) is a psychedelic phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin and is used as entheogenic recreational drug.

<span class="mw-page-title-main">2C-G</span> Chemical compound

2C-G is a psychedelic phenethylamine of the 2C-series. First synthesized by Alexander Shulgin, it is sometimes used as an entheogen. It has structural and pharmacodynamic properties similar to 2C-D and Ganesha. Like many of the phenethylamines in PiHKAL, 2C-G and its homologs have only been taken by Shulgin and a small test group, making it difficult to ensure completeness when describing effects.

<span class="mw-page-title-main">2,5-Dimethoxy-4-ethylamphetamine</span> 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.

Ganesha (2,5-dimethoxy-3,4-dimethylamphetamine) is a lesser-known psychedelic drug. It is also a substituted amphetamine. It was first synthesized by Alexander Shulgin. In his book PiHKAL, the dosage range is listed as 24–32 mg. The drug is usually taken orally, although other routes such as rectally may also be used. Ganesha is synthesized from 2,5-dimethoxy-3,4-dimethylbenzaldehyde. Ganesha is the amphetamine analog of 2C-G. It is a particularly long lasting drug, with the duration listed in PiHKAL as being 18–24 hours, which might make it undesirable to some users. It is named after the Hindu deity, Ganesha. Very little is known about the dangers or toxicity of ganesha. Effects of ganesha include:

<span class="mw-page-title-main">Aleph (psychedelic)</span> Chemical compound

Aleph is a psychedelic hallucinogenic drug and a substituted amphetamine of the phenethylamine class of compounds, which can be used as an entheogen. It was first synthesized by Alexander Shulgin, who named it after the first letter of the Hebrew alphabet. In his book PiHKAL, Shulgin lists the dosage range as 5–10 mg, with effects typically lasting for 6 to 8 hours.

<span class="mw-page-title-main">2C-T-15</span> Chemical compound

2C-T-15 or 2,5-dimethoxy-4-(β-cyclopropylthio)phenethylamine is a psychedelic phenethylamine of the 2C family. It was presumably first synthesized by Alexander Shulgin and reported in his book PiHKAL .

<span class="mw-page-title-main">HOT-2</span> Chemical compound

HOT-2 is a psychedelic phenethylamine of the 2C family. It was presumably first synthesized by Alexander Shulgin and reported in his book PiHKAL.

<span class="mw-page-title-main">HOT-7</span> Chemical compound

HOT-7, or 2,5-dimethoxy-4-(β-propylthio)-N-hydroxyphenethylamine, is a psychedelic phenethylamine of the 2C family. It was presumably first synthesized by Alexander Shulgin and reported in his book, PiHKAL.

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

3,4-Methylenedioxy-N-methoxyamphetamine is a lesser-known psychedelic drug and a substituted amphetamine. It is also the N-methoxy analogue of MDA. MDMEO was first synthesized by Alexander Shulgin. In his book PiHKAL , the minimum dosage is listed as 180 mg. MDMEO may be found as white crystals. It produces few to no effects. Very little data exists about the pharmacological properties, metabolism, and toxicity of MDMEO.

MDMEOET, or 3,4-methylenedioxy-N-methoxyethylamphetamine, is a lesser-known psychedelic drug and a substituted amphetamine. It is also the N-methoxyethyl analogue of MDA. MDMEOET was first synthesized by Alexander Shulgin. In his book PiHKAL , the minimum dosage is listed as 180 mg. MDMEOET produces few to no effects. Very little data exists about the pharmacological properties, metabolism, and toxicity of MDMEOET.

<span class="mw-page-title-main">3,4-Methylenedioxyphentermine</span> Chemical compound

3,4-Methylenedioxyphentermine (MDPH) is a lesser-known psychedelic drug. MDPH was first synthesized by Alexander Shulgin. In his book PiHKAL , the dosage range is listed as 160–240 mg, and the duration as 3–5 hours. MDPH's effects are very similar to those of MDA: they both are smooth and "stoning," and do not cause any visuals. They also alter dreams and dream patterns. Shulgin describes MDPH as a promoter; it promotes the effects of other drugs, similarly to 2C-D. Very little data exists about the pharmacological properties, metabolism, and toxicity of MDPH.

<span class="mw-page-title-main">3C-BZ</span> Chemical compound

3C-BZ (4-benzyloxy-3,5-dimethoxyamphetamine) is a lesser-known psychedelic drug and a substituted amphetamine. 3C-BZ was first synthesized by Alexander Shulgin. In his book PiHKAL, the dosage range is listed as 25–200 mg and the duration as 18–24 hours. According to anecdotal reports from the substance's entry in PiHKAL, 3C-BZ's effects can vary significantly, ranging from intensified emotions and strange dreams, to effects similar to those of LSD or TMA. Very little data exists about the pharmacological properties, metabolism, and toxicity of 3C-BZ.

<span class="mw-page-title-main">2C-H</span> Chemical compound

2C-H (2,5-dimethoxyphenethylamine) is a lesser-known substituted phenethylamine of the 2C family.

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

3,4-Methylenedioxy-N-hydroxy-N-methylamphetamine is an entactogen, psychedelic, and stimulant of the phenethylamine and amphetamine chemical classes. It is the N-hydroxy homologue of MDMA ("Ecstasy"), and the N-methyl homologue of MDOH. MDHMA was first synthesized and assayed by Alexander Shulgin. In his book PiHKAL, Shulgin listed the dosage range as 100–160 mg, and the duration as approximately 4–8 hours. He describes MDHMA as causing entactogenic and open MDMA-like effects, easing communication, and increasing appreciation of the senses.

<span class="mw-page-title-main">BOB (psychedelic)</span> Chemical compound

BOB (4-bromo-2,5,beta-trimethoxyphenethylamine) is a lesser-known psychedelic drug. It is the beta-methoxy analog of 2C-B. BOB was first synthesized by Alexander Shulgin. In his book PiHKAL, the dosage range is listed as 10–20 mg, and the duration listed as 10–20 hours. BOB produces an altered state of consciousness, tinnitus, a pleasant tingling throughout the body, and a sense of awareness. Very little data exists about the pharmacological properties, metabolism, and toxicity of BOB.

<span class="mw-page-title-main">BOHD (psychedelic)</span> Chemical compound

BOHD (4-methyl-2,5-dimethoxy-beta-hydroxyphenethylamine) is a lesser-known psychedelic drug. It is the beta-hydroxy derivative of 2C-D. BOHD was first synthesized by Alexander Shulgin. In his book PiHKAL, the minimum dosage is listed as 50 mg, and the duration unknown. BOHD produces a marked drop in blood pressure. Very little data exists about the pharmacological properties, metabolism, and toxicity of BOHD.

<span class="mw-page-title-main">2,5-Dimethoxy-4-methylphenylcyclopropylamine</span> Chemical compound

2,5-Dimethoxy-4-methylphenylcyclopropylamine (DMCPA) is a lesser-known psychedelic drug and a substituted amphetamine. DMCPA was first synthesized by Alexander Shulgin. In his book PiHKAL, the dosage range is listed as 15–20 mg and the duration is listed as 4–8 hours. DMCPA produces open-eye visuals, anorexia, and psychedelic dreams. Shulgin gives it a +++ on the Shulgin Rating Scale.

<span class="mw-page-title-main">DME (psychedelic)</span> Chemical compound

DME (3,4-dimethoxy-beta-hydroxyphenethylamine) is a lesser-known psychedelic drug. It is the beta-hydroxy derivative of 3,4-dimethoxyphenethylamine. DME was first synthesized by Alexander Shulgin. In his book PiHKAL, the minimum dosage is listed as 115 mg, and the duration unknown. DME produces few to no effects. Very little data exists about the pharmacological properties, metabolism, and toxicity of DME.

References

  1. 1 2 3 Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN   0-9630096-0-5. OCLC   25627628.
  2. "PiHKAL". isomerdesign.com. Retrieved 2012-03-17.
  3. Baltzly, Richard; Buck, Johannes S. (1940). "Amines Related to 2,5-Dimethoxyphenethylamine". Journal of the Chemical Society. 62: 161–164. doi:10.1021/ja01858a046.
  4. "§1308.11 Schedule I." Archived from the original on 2009-08-27. Retrieved 2014-12-21.
  5. 1 2 Poisons Standard October 2015 https://www.comlaw.gov.au/Details/F2015L01534
  6. "Misuse of Drugs Act 1975". New Zealand Government. Retrieved 2016-01-18.