ODMA (drug)

Last updated
ODMA
ODMA.svg
Clinical data
Other namesOxadiazolylmethamphetamine; Oxadiazolyl-N-methylamphetamine
Drug class Serotonin–norepinephrine–dopamine releasing agent; Entactogen; Stimulant
Identifiers
  • 1-(2,1,3-benzoxadiazol-5-yl)-N-methylpropan-2-amine
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
Formula C10H13N3O
Molar mass 191.234 g·mol−1
3D model (JSmol)
  • CC(CC1=CC2=NON=C2C=C1)NC
  • InChI=1S/C10H13N3O/c1-7(11-2)5-8-3-4-9-10(6-8)13-14-12-9/h3-4,6-7,11H,5H2,1-2H3
  • Key:BQJMJKZIZSBANE-UHFFFAOYSA-N

ODMA is a bioisosteric analogue of 3,4-methylenedioxy-N-methylamphetamine (MDMA) which was developed in an attempt to create an improved MDMA alternative for potential clinical use. [1] It is the analogue of MDMA in which the 1,3-benzodioxole ring has been replaced with a 2,1,3-benzoxadiazole ring. [1] TDMA and SeDMA are closely related analogues. [1] ODMA, TDMA, and SeDMA are releasing agents of serotonin, norepinephrine, and dopamine similarly to MDMA. [1] However, they are less potent and efficacious in activating the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors than MDMA and show differing and potentially improved metabolic and pharmacokinetic properties in comparison. [1] ODMA, TDMA, and SeDMA were first described in the scientific literature in June 2024. [1]

Contents

MDMA and 3,4-methylenedioxyamphetamine (MDA) are well-known serotonergic neurotoxins that damage serotonergic neurons in the brain. [2] [3] [4] [5] [6] However, MDMA and MDA injected directly into the brain have been found to not produce serotonergic neurotoxicity in rodents. [2] [7] [8] This suggests that peripherally formed metabolites of MDMA and MDA may be the actual mediators of the neurotoxicity rather than MDMA and MDA themselves. [2] [7] [8] ODMA, TDMA, and SeDMA, with the exception of N-demethylation, do not share any of the phase I or phase II metabolic pathways of MDMA. [1] Notably, in contrast to MDMA, methylenedioxy ring opening and consequent formation of catechol metabolites, which have been linked with free radical generation, does not occur. [1] As a result, ODMA, TDMA, and SeDMA might not share the serotonergic neurotoxicity of MDMA and MDA. [1] However, more research is needed to assess this possibility. [1] Moreover, other studies have found that slow infusion of MDMA directly into the brain does produce signs of serotonergic neurotoxicity. [9]

See also

Related Research Articles

<span class="mw-page-title-main">MDMA</span> Psychoactive drug, often called ecstasy

3,4-Methyl​enedioxy​methamphetamine (MDMA), commonly known as ecstasy, and molly, is an empathogen–entactogenic drug with stimulant and minor psychedelic properties. In studies, it has been used alongside psychotherapy in the treatment of post-traumatic stress disorder (PTSD) and social anxiety in autism spectrum disorder. The purported pharmacological effects that may be prosocial include altered sensations, increased energy, empathy, and pleasure. When taken by mouth, effects begin in 30 to 45 minutes and last three to six hours.

<span class="mw-page-title-main">Empathogen</span> Class of psychoactive drugs that produce empathic experiences

Empathogens or entactogens are a class of psychoactive drugs that induce the production of experiences of emotional communion, oneness, relatedness, emotional openness—that is, empathy or sympathy—as particularly observed and reported for experiences with 3,4-methylenedioxymethamphetamine (MDMA). This class of drug is distinguished from the classes of hallucinogen or psychedelic, and amphetamine or stimulants. Major members of this class include MDMA, MDA, MDEA, MDOH, MBDB, 5-APB, 5-MAPB, 6-APB, 6-MAPB, methylone, mephedrone, GHB, αMT, and αET, MDAI among others. Most entactogens are phenethylamines and amphetamines, although several, such as αMT and αET, are tryptamines. When referring to MDMA and its counterparts, the term MDxx is often used. Entactogens are sometimes incorrectly referred to as hallucinogens or stimulants, although many entactogens such as ecstasy exhibit psychedelic or stimulant properties as well.

<span class="mw-page-title-main">3,4-Methylenedioxyamphetamine</span> Empathogen-entactogen, psychostimulant, and psychedelic drug of the amphetamine family

3,4-Methylenedioxyamphetamine (MDA), sometimes referred to as “sass,” is an empathogen-entactogen, stimulant, and psychedelic drug of the amphetamine family that is encountered mainly as a recreational drug. In its pharmacology, MDA is a serotonin–norepinephrine–dopamine releasing agent (SNDRA). In most countries, the drug is a controlled substance and its possession and sale are illegal.

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

MBDB, also known as N-methyl-1,3-benzodioxolylbutanamine or as 3,4-methylenedioxy-N-methyl-α-ethylphenylethylamine, is an entactogen of the phenethylamine, amphetamine, and phenylisobutylamine families related to MDMA. It is known by the street names "Eden" and "Methyl-J".

<span class="mw-page-title-main">Methylone</span> Group of stereoisomers

Methylone, also known as 3,4-methylenedioxy-N-methylcathinone (MDMC), is an empathogen and stimulant psychoactive drug. It is a member of the amphetamine, cathinone and methylenedioxyphenethylamine classes.

<span class="mw-page-title-main">Substituted methylenedioxyphenethylamine</span> Class of psychoactive drugs

The substituted methylenedioxyphenethylamines represent a diverse chemical class of compounds derived from phenethylamines. This category encompasses numerous psychoactive substances with entactogenic, psychedelic, and/or stimulant properties, in addition to entheogens. These compounds find application as research chemicals, designer drugs, and recreational substances.

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

3,4-Ethylenedioxy-N-methylamphetamine (EDMA) is an entactogen drug of the methamphetamine class. It is an analogue of MDMA where the methylenedioxy ring has been replaced by an ethylenedioxy ring. EDMA was first synthesized by Alexander Shulgin. In his book PiHKAL, the dosage is listed as 150–250 mg, and the duration listed as 3–5 hours. According to Shulgin, EDMA produces a bare threshold consisting of paresthesia, nystagmus, and hypnogogic imagery, with few to no other effects.

<span class="mw-page-title-main">1,3-Benzodioxolylbutanamine</span> Enactogenic drug of the phenethylamine class

1,3-Benzodioxolylbutanamine is an entactogenic drug of the phenethylamine, amphetamine, and phenylisobutylamine families. It is the α-ethyl analog of MDPEA and MDA and the methylenedioxy analogue of α-ethylphenethylamine.

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

MDAI, also known as 5,6-methylenedioxy-2-aminoindane, is an entactogen drug of the 2-aminoindane group which is related to MDMA and produces similar subjective effects.

α-Methyldopamine Chemical compound

α-Methyldopamine (α-Me-DA), also known as 3,4-dihydroxyamphetamine or as catecholamphetamine, is a research chemical of the catecholamine and amphetamine families. It is a monoamine releasing agent and a metabolite of MDMA and MDA. The bis-glutathionyl metabolite of α-methyldopamine is slightly neurotoxic when directly injected into the brain's ventricles.

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

6,7-Methylenedioxy-2-aminotetralin (MDAT) is a drug developed in the 1990s by a team at Purdue University led by David E. Nichols. It appears to act as a serotonin releasing agent based on rodent drug discrimination assays comparing it to MDMA, in which it fully substitutes for, and additionally lacks any kind of serotonergic neurotoxicity. Hence, MDAT is considered likely to be a non-neurotoxic, putative entactogen in humans.

<span class="mw-page-title-main">4-Chlorophenylisobutylamine</span> Entactogen and stimulant drug of the phenethylamine class

4-Chlorophenylisobutylamine, also known as 4-chloro-α-ethylphenethylamine, is an entactogen and stimulant drug of the phenethylamine, amphetamine, and phenylisobutylamine families. It is an analogue of para-chloroamphetamine (PCA) where the alpha position methyl has been replaced with an ethyl group.

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

Difluoromethylenedioxyamphetamine is a substituted derivative of 3,4-methylenedioxyamphetamine (MDA), which was developed by Daniel Trachsel and coworkers, along with the corresponding fluorinated derivatives of MDMA, MDEA, BDB and MBDB, with the aim of finding a non-neurotoxic drug able to be used as a less harmful substitute for entactogenic drugs such as MDMA. Since a major route of the normal metabolism of these compounds is scission of the methylenedioxy ring, producing neurotoxic metabolites such as alpha-methyldopamine, it was hoped that the difluoromethylenedioxy bioisostere would show increased metabolic stability and less toxicity.

<span class="mw-page-title-main">5-MAPB</span> Chemical compound

5-MAPB, also known as 5-(N-methyl-2-aminopropyl)benzofuran, is an entactogen and designer drug of the amphetamine family that is similar to MDMA in its structure and effects.

<span class="mw-page-title-main">2,3-Methylenedioxymethamphetamine</span> Chemical compound

2,3-Methylenedioxymethamphetamine (2,3-MDMA) is a positional isomer of the recreational drug 3,4-MDMA.

<span class="mw-page-title-main">Monoamine neurotoxin</span> Compounds that damage or destroy monoaminergic neurons

A monoamine neurotoxin, or monoaminergic neurotoxin, is a drug that selectively damages or destroys monoaminergic neurons. Monoaminergic neurons are neurons that signal via stimulation by monoamine neurotransmitters including serotonin, dopamine, and norepinephrine.

<span class="mw-page-title-main">TDMA (drug)</span> MDMA analogue

TDMA is a bioisosteric analogue of 3,4-methylenedioxy-N-methylamphetamine (MDMA) which was developed in an attempt to create an improved MDMA alternative for potential clinical use. It is the analogue of MDMA in which the 1,3-benzodioxole ring has been replaced with a 2,1,3-benzothiadiazole ring. ODMA and SeDMA are closely related analogues. ODMA, TDMA, and SeDMA are releasing agents of serotonin, norepinephrine, and dopamine similarly to MDMA. However, they are less potent and efficacious in activating the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors than MDMA and show differing and potentially improved metabolic and pharmacokinetic properties in comparison. ODMA, TDMA, and SeDMA were first described in the scientific literature in June 2024.

<span class="mw-page-title-main">SeDMA</span> MDMA analogue

SeDMA is a bioisosteric analogue of 3,4-methylenedioxy-N-methylamphetamine (MDMA) which was developed in an attempt to create an improved MDMA alternative for potential clinical use. It is the analogue of MDMA in which the 1,3-benzodioxole ring has been replaced with a 2,1,3-benzoselenadiazole ring. ODMA and TDMA are closely related analogues. ODMA, TDMA, and SeDMA are releasing agents of serotonin, norepinephrine, and dopamine similarly to MDMA. However, they are less potent and efficacious in activating the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors than MDMA and show differing and potentially improved metabolic and pharmacokinetic properties in comparison. ODMA, TDMA, and SeDMA were first described in the scientific literature in June 2024.

<span class="mw-page-title-main">3,4-Dihydroxymethamphetamine</span> MDMA metabolite

3,4-Dihydroxymethamphetamine, or 3,4-dihydroxy-N-methylamphetamine, also known as α-methylepinine or α,N-dimethyldopamine, is the major metabolite of 3,4-methylenedioxy-N-methylamphetamine (MDMA). It is formed from MDMA by O-demethylation via cytochrome P450 enzymes including CYP2D6 as well as CYP1A2 and CYP3A4. Like MDMA, HHMA is a monoamine releasing agent.

<span class="mw-page-title-main">Borax combo</span> Designer drug

The Borax combo, also known by the informal brand names Blue Bliss and Pink Star, is a combination recreational and designer drug that is anecdotally claimed to closely mimic the effects and "magic" of the entactogen MDMA ("ecstasy"). It is a mixture of three distinct drugs with different mechanisms of action and employed at specific fixed doses:

  1. 5-MAPB, an entactogen acting as a well-balanced serotonin–norepinephrine–dopamine releasing agent (SNDRA)
  2. 2-Fluoromethamphetamine (2-FMA), an amphetamine-like psychostimulant and probable norepinephrine–dopamine releasing agent (NDRA)
  3. 5-MeO-MiPT or 4-HO-MET, serotonergic psychedelics and non-selective serotonin receptor agonists

References

  1. 1 2 3 4 5 6 7 8 9 10 Alberto-Silva AS, Hemmer S, Bock HA, da Silva LA, Scott KR, Kastner N, Bhatt M, Niello M, Jäntsch K, Kudlacek O, Bossi E, Stockner T, Meyer MR, McCorvy JD, Brandt SD, Kavanagh P, Sitte HH (June 2024). "Bioisosteric analogs of MDMA: Improving the pharmacological profile?". J Neurochem. 168 (9): 2022–2042. doi:10.1111/jnc.16149. PMC  11449655. PMID   38898705.
  2. 1 2 3 Costa G, Gołembiowska K (January 2022). "Neurotoxicity of MDMA: Main effects and mechanisms". Exp Neurol. 347: 113894. doi:10.1016/j.expneurol.2021.113894. hdl: 11584/325355 . PMID   34655576.
  3. ↑ Kostrzewa RM (2022). "Survey of Selective Monoaminergic Neurotoxins Targeting Dopaminergic, Noradrenergic, and Serotoninergic Neurons". Handbook of Neurotoxicity. Cham: Springer International Publishing. pp. 159–198. doi:10.1007/978-3-031-15080-7_53. ISBN   978-3-031-15079-1.
  4. ↑ Parrott AC (September 2013). "MDMA, serotonergic neurotoxicity, and the diverse functional deficits of recreational 'Ecstasy' users". Neurosci Biobehav Rev. 37 (8): 1466–1484. doi:10.1016/j.neubiorev.2013.04.016. PMID   23660456.
  5. ↑ Aguilar MA, García-Pardo MP, Parrott AC (January 2020). "Of mice and men on MDMA: A translational comparison of the neuropsychobiological effects of 3,4-methylenedioxymethamphetamine ('Ecstasy')". Brain Res. 1727: 146556. doi:10.1016/j.brainres.2019.146556. PMID   31734398.
  6. ↑ Montgomery C, Roberts CA (January 2022). "Neurological and cognitive alterations induced by MDMA in humans" (PDF). Exp Neurol. 347: 113888. doi:10.1016/j.expneurol.2021.113888. PMID   34624331.
  7. 1 2 Monks TJ, Jones DC, Bai F, Lau SS (April 2004). "The role of metabolism in 3,4-(+)-methylenedioxyamphetamine and 3,4-(+)-methylenedioxymethamphetamine (ecstasy) toxicity". Ther Drug Monit. 26 (2): 132–136. doi:10.1097/00007691-200404000-00008. PMID   15228153.
  8. 1 2 Esteban B, O'Shea E, Camarero J, Sanchez V, Green AR, Colado MI (March 2001). "3,4-Methylenedioxymethamphetamine induces monoamine release, but not toxicity, when administered centrally at a concentration occurring following a peripherally injected neurotoxic dose". Psychopharmacology (Berl). 154 (3): 251–260. doi:10.1007/s002130000645. PMID   11351932.
  9. ↑ Baggott, Matthew; Mendelson, John (2001). "Does MDMA Cause Brain Damage?". In Holland, J. (ed.). Ecstasy: The Complete Guide: A Comprehensive Look at the Risks and Benefits of MDMA. Inner Traditions/Bear. pp. 110–145, 396–404. ISBN   978-0-89281-857-0 . Retrieved 24 November 2024. While a single injection of MDMA into the brain (intracerebroventricularly) had no effect on TPH activity, slow infusion of 1 mg/kg MDMA into the brain over 1 hr produced enough oxidative stress to acutely reduce TPH activity (Schmidt and Taylor 1988). The acute decrease in TPH activity is an early effect of MDMA and can be measured at post 15 min (Stone et al. 1989b). TPH inactivation can also be produced by non-neurotoxic MDMA doses (Schmidt and Taylor 1988; Stone et al. 1989a; Stone et al. 1989b). It therefore appears that MDMA rapidly induces oxidative stress but only produces neurotoxicity when endogenous free radical scavenging systems are overwhelmed.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.