3,4-methylenedioxyamphetamine
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| 1: 1 mixture of enantiomers : ( R ) -form (top) and ( S ) -form (bottom) | |||||||||||||
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| Surname | 3,4-methylenedioxyamphetamine | ||||||||||||
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| Molecular formula | C 10 H 13 NO 2 | ||||||||||||
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| properties | |||||||||||||
| Molar mass | 179.22 g · mol -1 | ||||||||||||
| Physical state |
firmly |
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| Melting point |
187–188 ° C (racemate hydrochloride) |
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| boiling point |
157 ° C (at 22 h Pa , racemate, free base) |
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | |||||||||||||
3,4-methylenedioxyamphetamine , or MDA for short , is a synthetic hallucinogenic drug that is banned in many countries. Chemically and structurally, MDA belongs to the group of amphetamines , more precisely methylenedioxyamphetamines .
history
MDA was first synthesized in 1910 by chemists Carl Mannich (1877–1947) and Willy Jacobsohn (1884–1963) at Merck in Darmstadt.
From 1962, the US chemist Alexander Shulgin carried out self- experiments with the substance.
From the late 1960s , MDA was then widespread in the hippie scene as a so-called hug drug (cuddle drug ). Alluding to it was used as M ellow D rug of A designated merica (America's soft drug).
After the effect of the related active ingredient MDMA became known from the 1970s at the latest, MDA, u. a. Due to the weaker empathogenic effect, at least used as a party drug less than MDMA, but otherwise went through a parallel development until today. MDA was used in psychotherapy until it was banned in the 1980s , as the drug also promotes the tendency to open up to the therapist more easily and to gain deeper insights into one's own psyche. And even today, MDA is often contained in ecstasy pills instead of or in addition to MDMA.
synthesis
The production is usually done using the raw material piperonal . In PIHKAL the preparation via the nitropropene (piperonal + nitroethane) and reduction with is LAH described. It is also a possible starting material in the synthesis of MDMA . Another possible synthesis route is via the natural product safrole with subsequent halogenation and subsequent substitution with ammonia . An alternative synthetic route goes from isosafrole via 3,4-methylenedioxyphenylacetone to MDA.
Chemical and pharmacological properties
There are two pharmacologically active enantiomers , the ( R ) form and the mirror image ( S ) form of the active ingredient. The free base MDA is an oil and contains the functional group of a primary amine R – NH 2. The free base forms a crystalline hydrochloride R – NH 2 · HCl with hydrochloric acid .
MDA has a slightly hallucinogenic , entactogenic and (in contrast to MDMA) weaker empathogenic effect. MDA causes the release of catecholamine neurotransmitters and increases the intensity of emotions. Often people under the influence of MDA tend to philosophize, have an increased need to speak and experience an increased I-experience. MDA simulates that the consumer has both physical and mental stamina.
The effective dosage is in the range from 80 to 160 mg, the duration of action is between four and twelve hours. MDA is a breakdown product of MDMA.
hazards
The dangers of long-term consumption of MDA, like those of MDMA, have not been finally clarified. Permanent damage to the central nervous system is suspected . There are no long-term human studies yet; possible long-term damage is suspected above all in the neurons in the cerebral cortex , hippocampus , striatum , hypothalamus and in the midbrain . However, MDA is considered to be more neurotoxic than MDMA, MDE, and MBDB.
Legal status
MDA was introduced by the UN's Narcotics Control Council in Schedule I of the Convention on Psychotropic Substances and is therefore practically illegal worldwide.
In the Federal Republic of Germany , MDA was included as a non-marketable narcotic drug in Appendix 1 to Section 1 (1) BtMG with the first Narcotics Law Amendment Ordinance (1st BtMÄndV) of 6 August 1984 ( BGBl. 1984 I p. 1081) .
Since 1998, all amphetamines in the BtMG and BtMVV have been written with f instead of ph . MDA is also referred to as tenamfetamine in the BtMG . The spelling has thus been adapted to the WHO nomenclature.
literature
- Claudio Naranjo : The journey to the self. Psychotherapy with healing drugs. Treatment protocols. Translated from American English by Modeste zur Nedden-Pferdekamp. Fischer, Frankfurt am Main 1979, ISBN 3-596-23381-X .
Web links
Individual evidence
- ↑ T. Passie, U. Benzenhöfer: MDA, MDMA, and other "mescaline-like" substances in the US military's search for a truth drug (1940s to 1960s). In: Drug testing and analysis. Volume 10, number 1, January 2018, pp. 72-80, doi : 10.1002 / dta.2292 , PMID 28851034 (review).
- ↑ a b 3,4-Methylenedioxyamphetamine . In: The Merck Index : An Encyclopedia of Chemicals, Drugs, and Biologicals . 14th edition. Merck & Co., Whitehouse Station NJ 2006, ISBN 978-0-911910-00-1 , pp. 995-996.
- ↑ a b Data sheet (±) -3,4-Methylenedioxyamphetamine hydrochloride from Sigma-Aldrich , accessed on March 20, 2011 ( PDF ).
- ↑ beta-3,4-Methylenedioxyphenylisopropylamine (MDA) - [www.rhodium.ws ] .
- ↑ C. Mannich, W. Jacobsohn, C. Mannich: About Oxyphenyl-alkylamine and Dioxyphenyl-alkylamine. In: Reports of the German Chemical Society. 43, 1910, p. 189, doi : 10.1002 / cber.19100430126 .
- ↑ Shulgin, Alexander and Ann Shulgin (1995): PIHKAL - A Chemical Love Story. Transform Press , section on MDA , accessed October 8, 2015.
- ↑ Julie Holland (2001): Ecstasy - The Complete Guide: A Comprehensive Look at the Risks and Benefits of MDMA , page 11, Park Street Press, ISBN 9780892818570 .
- ↑ Erowid Online Books: "PIHKAL" - # 100 MDA .
- ↑ a b MDA (3,4 methylenedioxyamphetamine). In: drogen-info-berlin.de. Retrieved May 20, 2016 .
- ^ 1. BtMÄndV of August 6, 1984 .
- ↑ Appendix I to § 1 BtMG .
- ↑ 10. BtMÄndV Art. 1 No. 1 letter b .
