Methiopropamine
Methiopropamine is a synthetic stimulant of the thiophene class and a structural analogue of methamphetamine, first synthesized in 1942.1 Despite this structural similarity, it is neither an amphetamine nor a phenethylamine, as it features a thiophene ring in place of a benzene ring. It entered recreational drug markets around 2010 as a research chemical and legal high. Methiopropamine is generally characterized as a functional stimulant with limited euphoric properties.
Contents
Dosage & Duration
Dosage
Duration
Subjective Effects
Effects vary widely by individual, dose, and context.
Physical
The physical effects of methiopropamine can be broken down into several components which progressively intensify proportional to dosage.
Cognitive
The cognitive effects of methiopropamine can be broken down into several components which progressively intensify proportional to dosage. It contains a large number of typical stimulant cognitive effects. Although negative side effects are usually mild at low to moderate doses, they become increasingly likely to manifest themselves with higher amounts or extended usage. This particularly holds true during the offset of the experience.
Reagent Testing
Loading reagent data
Pharmacology
Pharmacodynamics
Methiopropamine acts primarily as a norepinephrine-dopamine reuptake inhibitor (NDRI), with approximately 1.85 times greater selectivity for norepinephrine over dopamine. Compared to dextroamphetamine, it is roughly one-third as potent at inhibiting norepinephrine reuptake and one-fifth as potent at inhibiting dopamine reuptake. It may additionally function as a monoamine releasing agent, though this has not been definitively established. It displays negligible activity at the serotonin transporter.2
Pharmacokinetics
Methiopropamine is metabolized primarily through N-demethylation and hydroxylation at the side chain or thiophene ring. CYP2C19 catalyzes further deamination of the N-demethylated metabolites in the liver, producing the inactive compound 1-(thiophen-2-yl)-2-propan-2-one. Thiophene-2-carboxylic acid is the final major metabolic product and is excreted renally. Both methiopropamine and its active metabolite thiopropamine are also excreted unchanged in urine.
Dangerous
Highest riskThese combinations are considered extremely harmful and should always be avoided. Reactions to these drugs taken in combination are highly unpredictable and have a potential to cause death.
Tolerance
Dopaminergic stimulants
Harm Potential
Addiction & Dependence
Psychological
ModerateModerately addictive with high potential for abuse and capable of causing psychological dependence. Compulsive redosing is commonly reported, particularly with insufflation or vaporization routes, though generally considered less severe than substances like MDPV or mephedrone.
Physical
LowCravings and withdrawal effects may occur following cessation of chronic use, though physical dependence appears less prominent than psychological dependence.
Toxicity
Cardiovascular stimulation including chest tightness, chest pains, racing heart, vasoconstriction, and palpitations are somewhat common at higher doses and with repeated dosing; serious cardiovascular events appear to be associated with overdose or extreme use patterns rather than typical recreational use.
Labored breathing and pain with deep breaths have been reported, primarily at higher doses or with repeated dosing.
Psychosis Risk
Capable of producing stimulant psychosis with symptoms including paranoia, visual and auditory hallucinations, delusions, and incoherent speech.12 Risk is significantly elevated by high doses, repeated dosing, and accompanying sleep deprivation. Case reports document paranoid delusions, dysmorphophobia, and self-harming behavior in affected users.
History & Culture
Discovery and Early Research
Methiopropamine was first synthesized and reported in 1942.3 The work was primarily conducted at the University of Michigan, with limited pharmacological evaluation carried out at Parke Davis pharmaceutical company. This early research demonstrated that the compound possessed
Legality
By Country
References
Source Pages
Citations
- Wood, Dargan, Smit, Archer, Köpp, Baker, Kavanagh, Dines, Yip, Greene, Ghodse, & Ramsey. (2014). Acute Toxicity Associated with Analytically Confirmed Recreational use of Methiopropamine (1-(thiophen-2-yl)-2-methylaminopropane). Journal of Medical Toxicology, 10(3), 299-302. https://doi.org/10.1007/s13181-014-0399-y12
- Torrente S.S., & et al.. (2021). Comparative Neuropharmacology and Pharmacokinetics of Methamphetamine and Its Thiophene Analog Methiopropamine in Rodents. International Journal of Molecular Sciences. https://doi.org/10.3390/ijms22211200212
- Advisory Council on the Misuse of Drugs. (2017). Methiopropamine (MPA): A review of the evidence of use and harm — Further advice, June 2017. UK Home Office / ACMD. https://assets.publishing.service.gov.uk/media/5a81c10140f0b62302698fb3/ACMD_s_further_advice_on_methiopropamine_June_2017.pdf12
- (n.d.). Methiopropamine — Office of Drug Control controlled-substances list. Office of Drug Control. https://www.odc.gov.au/controlled-substances/list/methiopropamine1
- (2015-11-23). The Misuse of Drugs Act 1971 (Temporary Class Drug) (No. 3) Order 2015. legislation.gov.uk, Article SI 2015/1929. https://www.legislation.gov.uk/uksi/2015/1929/made1
- (2017). Circular 011/2017: A change to the Misuse of Drugs Act 1971 to control Methiopropamine (MPA). GOV.UK. https://www.gov.uk/government/publications/circular-0112017-a-change-to-the-misuse-of-drugs-act-1971-to-control-methiopropamine-mpa/circular-0112017-a-change-to-the-misuse-of-drugs-act-1971-to-control-methiopropamine-mpa1
- Drug Enforcement Administration. (2022-12-09). Schedules of Controlled Substances: Placement of Methiopropamine in Schedule I. Federal Register, Article 2022-26805. https://www.federalregister.gov/documents/2022/12/09/2022-26805/schedules-of-controlled-substances-placement-of-methiopropamine-in-schedule-i1
Further Reading
Automated synthesisInformation aggregated and synthesized using an autonomous workflow built by Josie Kins.
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