View source for Trimethoxyamphetamine

'''TMAs''', also known as '''trimethoxyamphetamines''', are a family of [[isomer]]ic [[psychedelic]] [[hallucinogenic drug|hallucinogenic]] [[psychoactive drug|drugs]]. There exist six different TMAs that differ only in the position of the three [[methoxy]] [[Functional group|groups]]: TMA, TMA-2, TMA-3, TMA-4, TMA-5, and TMA-6. The TMAs are analogs of the [[phenethylamine]] [[cactus]] [[alkaloid]] [[mescaline]]. The TMAs are [[substituted amphetamine]]s, however, their action does not resemble that of the unsubstituted compound ''amphetamine'', which is a [[stimulant]] and not a psychedelic. It is reported that some TMA's elicit a range of emotions ranging from sadness to empathy and euphoria. Several TMAs were first [[Chemical synthesis|synthesized]] by the chemist [[Alexander Shulgin]]. Synthesis data as well as [[human]] activity data has been published in the book ''[[PiHKAL|PiHKAL (Phenethylamines i Have Known And Loved)]]''. 

The most important TMA compound from a pharmacological standpoint is TMA-2, as this isomer has been much more widely used as a recreational drug and sold on the black market and as a "[[research chemical]]"; TMA (sometimes referred to as "mescalamphetamine") and TMA-6 have also been used in this way to a lesser extent. These three isomers are significantly more active as hallucinogenic drugs, and have consequently been placed onto the illegal drug schedules in some countries such as the [[Netherlands]] and [[Japan]]. The other three isomers TMA-3, TMA-4 and TMA-5 are not known to have been used as recreational drugs to any great extent, and remain obscure scientific curiosities. 

== TMAs ==

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<table><tr><td>
{| border="1" cellpadding="2" cellspacing="0" align="right" style="margin: 0 0 1em 1em; float: right;"
! colspan="2" align=center bgcolor="#cccccc" | '''TMA'''
|-
| [[IUPAC nomenclature|Chemical name]]
| 1-(3,4,5-Trimethoxyphenyl)propan-2-amine,<br/>3,4,5-trimethoxyamphetamine
|-
| [[Melting point]]
| 220 - 221 °C (hydrochloride)
|-
| [[Simplified molecular input line entry specification|SMILES]]
| <small>NC(C)CC1=CC(OC)=C(OC)C(OC)=C1</small>
|-
| [[CAS registry number|CAS number]]<br>1082-88-8 || <center>[[Image:Trimethoxyamphetamine structure.svg|152px|Chemical structure of TMA]]<center/>
|-
|}</td><td>
{| border="1" cellpadding="2" cellspacing="0" align="right" style="margin: 0 0 1em 1em; float: right;"
! colspan="2" align=center bgcolor="#cccccc" | '''TMA-2'''
|-
| [[IUPAC nomenclature|Chemical name]]
| 1-(2,4,5-Trimethoxyphenyl)propan-2-amine,<br/>2,4,5-trimethoxyamphetamine
|-
| [[Melting point]]
| 188.5 - 189.5 °C (hydrochloride)
|-
| [[Simplified molecular input line entry specification|SMILES]]
| <small>NC(C)CC1=C(OC)C=C(OC)C(OC)=C1</small>
|-
| [[CAS registry number|CAS number]]<br>1083-09-6 || <center>[[Image:Trimethoxyamphetamine-2.svg|152px|Chemical structure of TMA-2]]</center>
|-
|}</td><td>
{| border="1" cellpadding="2" cellspacing="0" align="right" style="margin: 0 0 1em 1em; float: right;"
! colspan="2" align=center bgcolor="#cccccc" | '''TMA-3'''
|-
| [[IUPAC nomenclature|Chemical name]]
| 1-(2,3,4-Trimethoxyphenyl)propan-2-amine,<br/>2,3,4-trimethoxyamphetamine
|-
| [[Melting point]]
| 148 - 149 °C (hydrochloride)
|-
| [[Simplified molecular input line entry specification|SMILES]]
| <small>NC(C)CC1=CC=C(OC)C(OC)=C1OC</small>
|-
| [[CAS registry number|CAS number]]<br>1082-23-1 || <center>[[Image:Trimethoxyamphetamine-3.svg|154px|Chemical structure of TMA-3]]</center>
|-
|}</td></tr><tr><td>
{| border="1" cellpadding="2" cellspacing="0" align="right" style="margin: 0 0 1em 1em; float: right;"
! colspan="2" align=center bgcolor="#cccccc" | '''TMA-4'''
|-
| [[IUPAC nomenclature|Chemical name]]
| 1-(2,3,5-Trimethoxyphenyl)propan-2-amine,<br/>2,3,5-trimethoxyamphetamine
|-
| [[Melting point]]
| 118 - 119 °C (hydrochloride)
|-
| [[Simplified molecular input line entry specification|SMILES]]
| <small>NC(C)CC1=CC(OC)=CC(OC)=C1OC</small>
|-
| [[CAS registry number|CAS number]]<br>23693-14-3 || <center>[[Image:Trimethoxyamphetamine-4.svg|153px|Chemical structure of TMA-4]]</center>
|-
|}</td><td>
{| border="1" cellpadding="2" cellspacing="0" align="right" style="margin: 0 0 1em 1em; float: right;"
! colspan="2" align=center bgcolor="#cccccc" | '''TMA-5'''
|-
| [[IUPAC nomenclature|Chemical name]]
| 1-(2,3,6-Trimethoxyphenyl)propan-2-amine,<br/>2,3,6-trimethoxyamphetamine
|-
| [[Melting point]]
| 124 - 125 °C (hydrochloride)
|-
| [[Simplified molecular input line entry specification|SMILES]]
| <small>NC(C)CC1=C(OC)C=CC(OC)=C1OC</small>
|-
| [[CAS registry number|CAS number]]<br>20513-16-0 || <center>[[Image:Trimethoxyamphetamine-5.svg|118px|Chemical structure of TMA-5]]</center>
|-
|}</td><td>
{| border="1" cellpadding="2" cellspacing="0" align="right" style="margin: 0 0 1em 1em; float: right;"
! colspan="2" align=center bgcolor="#cccccc" | '''TMA-6'''
|-
| [[IUPAC nomenclature|Chemical name]]
| 1-(2,4,6-Trimethoxyphenyl)propan-2-amine,<br/>2,4,6-trimethoxyamphetamine
|-
| [[Melting point]]
| 207 - 208 °C (hydrochloride)
|-
| [[Simplified molecular input line entry specification|SMILES]]
| <small>NC(C)CC1=C(OC)C=C(OC)C=C1OC</small>
|-
| [[CAS registry number|CAS number]]<br>15402-79-6 || <center>[[Image:Trimethoxyamphetamine-6.svg|152px|Chemical structure of TMA-6]]</center>
|-
|}</td></tr></table>
<br clear="both">

== Chemical data ==

As they are isomers the TMAs have the same [[Chemical formula|totals formula]], C<sub>12</sub>H<sub>19</sub>NO<sub>3</sub>, and the same [[molecular mass]], 225.28 g/mol.

== Properties ==

{| border="1" cellspacing="0" cellpadding="3" style="background: #ffffff; border-collapse: collapse; margin-left: auto; margin-right: auto;"
|- bgcolor="#eeeeee" align="center"
!                     Compound    || Pattern || Dose          || Duration
|- align="center"
| bgcolor="#eeeeee" | '''TMA'''   || 3,4,5   || 100 – 250&nbsp;mg  || 6 - 8 h
|- align="center"
| bgcolor="#eeeeee" | '''TMA-2''' || 2,4,5   || 20 – 40&nbsp;mg    || 8 - 12 h
|- align="center"
| bgcolor="#eeeeee" | '''TMA-3''' || 2,3,4   || > 100&nbsp;mg      || ''unknown''
|- align="center"
| bgcolor="#eeeeee" | '''TMA-4''' || 2,3,5   || 80&nbsp;mg         || ~ 6 h
|- align="center"
| bgcolor="#eeeeee" | '''TMA-5''' || 2,3,6   || ≥ 30&nbsp;mg || 8 - 10 h
|- align="center"
| bgcolor="#eeeeee" | '''TMA-6''' || 2,4,6   || 25 – 50&nbsp;mg    || 12 - 16 h 
|-
|}

== See also ==
* [[Psychedelic]]
* [[Hallucinogenic drug]]
* [[Phenethylamine]]s
* [[Amphetamine]]s
* [[Recreational drug use]]
* [[2,5-Dimethoxy-4-Substituted Amphetamine]]s

== External links ==
* PiHKAL entries:
** [http://www.erowid.org/library/books_online/pihkal/pihkal157.shtml TMA]
** [http://pihkal.info/read.php?domain=pk&id=157 TMA in PiHKAL • info]
** [http://www.erowid.org/library/books_online/pihkal/pihkal158.shtml TMA-2]
** [http://pihkal.info/read.php?domain=pk&id=158 TMA-2 in PiHKAL • info]
** [http://www.erowid.org/library/books_online/pihkal/pihkal159.shtml TMA-3]
** [http://pihkal.info/read.php?domain=pk&id=159 TMA-3 in PiHKAL • info]
** [http://www.erowid.org/library/books_online/pihkal/pihkal160.shtml TMA-4]
** [http://pihkal.info/read.php?domain=pk&id=160 TMA-4 in PiHKAL • info]
** [http://www.erowid.org/library/books_online/pihkal/pihkal161.shtml TMA-5]
** [http://pihkal.info/read.php?domain=pk&id=161 TMA-5 in PiHKAL • info]
** [http://www.erowid.org/library/books_online/pihkal/pihkal162.shtml TMA-6]
** [http://pihkal.info/read.php?domain=pk&id=162 TMA-6 in PiHKAL • info]
* [http://www.erowid.org/chemicals/tma2/tma2.shtml Erowid TMA vault]
* [http://www.emcdda.europa.eu/index.cfm?fuseaction=public.Content&nNodeID=431 EMCDDA Report on the risk assessment of TMA-2 in the framework of the joint action on new synthetic drugs]

== References ==
{{Reflist|2}}

{{Hallucinogens}}
{{Serotonergics}}
{{Phenethylamines}}

[[Category:Amphetamine alkaloids]]
[[Category:Phenol ethers]]

[[de:Trimethoxyamphetamin]]
[[fr:Triméthoxyamphétamine]]
[[nl:Trimethoxyamfetamine]]
[[pl:Trimetoksyamfetaminy]]
[[ru:3,4,5-триметоксиамфетамин]]
[[Category:2Fix]]