Methiopropamine
 |
|
|---|---|
| Systematic (IUPAC) name | |
| 1-(thiophen-2-yl)-2-methylaminopropane | |
| Clinical data | |
| Pregnancy cat. | ? |
| Legal status | ? |
| Pharmacokinetic data | |
| Metabolism | liver |
| Half-life | a few hours[1] |
| Identifiers | |
| CAS number | 801156-47-8  7464-94-0 (hydrochloride) |
| ATC code | N06AA |
| PubChem | CID 436156 |
| ChemSpider | 385727  |
| Chemical data | |
| Formula | C8H13NS |
| Mol. mass | 155.261 g/mol |
|
|
|
|
 (what is this?) (verify) |
Methiopropamine (MPA) is a thiophene ring-based structural analog of methamphetamine originally reported in 1942.[2] Chemically it is not a phenethylamine or amphetamine and is not their functional analog either. It originally appeared for public sale in the UK in December 2010 as a "research chemical" or "legal high", recently branded as Blow.[3] It gained limited popularity as a recreational stimulant due to its relatively mild euphoria in comparison to other common stimulants like amphetamine, instead being described as clear headed,[1] a more functional stimulant[citation needed]
Long term health risks are yet to be determined due to lack of interest from the pharmaceutical industry in terms of testing the substance, and anecdotal data from recreational users is also limited.
Contents |
[edit] Anecdotal reports
Due to a lack of clinical studies, only anecdotal reports exist for its effects. Anecdotal reports from internet forums of subjective effects include mild euphoria, increased alertness, energy and focus,[citation needed] and sexual arousal. Reported negative effects include increased heart rate, loss of appetite, psychological addiction, vasoconstriction, anxiety, difficulty urinating, labored breathing, chestpain and significant hangover after extended use (nausea, headache, dizziness, lack of energy).[1] A number of users have also reported stomach complaints after using,[citation needed] particularly after re-dosing.[citation needed]
Ancedotal reports have also included reporting it to have much more prominent negative side effects compared to common stimulants like amphetamine.[citation needed]
Methiopropamine has good and almost equal bioavailability when taken orally, insufflated or vaporized.[citation needed] Total duration of experience is listed ~3 hours. After effects linger for 8–18 hours.[1]
[edit] Metabolism
The elimination process of the N-alkyl amphetamine from the body, the metabolic processes, deamination and N-dealkylation are the major pathways and the renal excretion is the minor one.[4] Methiopropamine is metabolized into active thiopropamine, 4-hydroxymethiopropamine and thiophene S-oxides.[5][6] These N-demethylated metabolites are further deaminated by CYP2C in liver transforming them into inactive 1-(thiophen-2-yl)-2-propan-2-one which can be seen as a phenylacetone derivative.[7]
Thiophene-2-carboxylic acid should be the final major metabolic product. It is very hydrophilic and is excreteted in urine. Methiopropamine and especially thiopropamine are also excreteted renally unchanged, likely to a significant portion.
[edit] Dosage
Methiopropamine dose ranges from 10 mg–50 mg regardless of route of administration. It can be taken by oral, insufflated, vaporized or rectal.[1]
[edit] Synthesis
There is a four step synthesis of methiopropamine. It begins with (thiophen-2-yl)magnesium bromide, which is reacted with propylene oxide, yielding 1-(thiophen-2-yl)-2-hydroxypropane which is reacted with phosphorus tribromide, yielding 1-(thiophen-2-yl)-2-bromopropane which is finally reacted with methylamine, yielding 1-(thiophen-2-yl)-2-methylaminopropane.[8]
[edit] See also
- Thiopropamine, demethylated counterpart.
- Propylhexedrine, another ring substituted stimulant. Used as over-the-counter decongestant.
[edit] References
- ^ a b c d e "Methiopropamine Vault". Erowid. 2011-07-05. Retrieved 2012-03-01.
- ^ Blicke, F. F.; Burckhalter, J. H. (1942). "α-Thienylaminoalkanes". Journal of the American Chemical Society 64 (3): 477–80. doi:10.1021/ja01255a001.
- ^ Angelov, D; O'Brien, J; Kavanagh, P (2011). "The syntheses of 1-(2-thienyl)-2-(methylamino) propane (methiopropamine) and its 3-thienyl isomer for use as reference standards". Drug testing and analysis: n/a. doi:10.1002/dta.298. PMID 21770051.
- ^ Vree, T.B.; Gorgels, J.P.M.C.; Muskens, A.Th.J.M.; Van Rossum, J.M. (1971). "Deuterium isotope effects in the metabolism of n-alkylsubstituted amphetamines in man". Clinica Chimica Acta 34 (2): 333–44. doi:10.1016/0009-8981(71)90187-2. PMID 5113570.
- ^ Treiber, Alexander; Dansette, Patrick M.; El Amri, Hamid; Girault, Jean-Pierre; Ginderow, Daria; Mornon, Jean-Paul; Mansuy, Daniel (1997). "Chemical and Biological Oxidation of Thiophene: Preparation and Complete Characterization of Thiophene S-Oxide Dimers and Evidence for Thiophene S-Oxide as an Intermediate in Thiophene Metabolism in Vivo and in Vitro". Journal of the American Chemical Society 119 (7): 1565–71. doi:10.1021/ja962466g.
- ^ Dansette, P.M.; Thang, Do Cao; Mansuy, H. El Amri D.; Mansuy, D (1992). "Evidence for thiophene-s-oxide as a primary reactive metabolite of thiophene in vivo: Formation of a dihydrothiophene sulfoxide mercapturic acid". Biochemical and Biophysical Research Communications 186 (3): 1624–30. doi:10.1016/S0006-291X(05)81594-3. PMID 1510686.
- ^ Yamada, Hideyuki; Shiiyama, Sachiko; Soejimaohkuma, Toyomi; Honda, Shin-Ichiro; Kumagai, Yoshito; Cho, Arthur K.; Oguri, Kazuta; Yoshimura, Hidetoshi (1997). "Deamination of amphetamines by cytochromes P450: Studies on substrate specificity and regioselectivity with microsomes and purified CYP2C subfamily isozymes". The Journal of Toxicological Sciences 22 (1): 65–73. doi:10.2131/jts.22.65. PMID 9076658.
- ^ Casale, John F.; Hays, Patrick A. (2011). "Methiopropamine: An Analytical Profile". Microgram Journal 8 (2): 53–7.
