N-t-BOC-MDMA

Last updated
N-t-BOC-MDMA
TBOC-MDMA structure.png
Identifiers
  • tert-Butyl N-[1-(1,3-benzodioxol-5-yl)propan-2-yl]-N-methylcarbamate
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
Formula C16H23NO4
Molar mass 293.363 g·mol−1
3D model (JSmol)
  • CC(CC1=CC2=C(C=C1)OCO2)N(C)C(=O)OC(C)(C)C
  • InChI=1S/C16H23NO4/c1-11(17(5)15(18)21-16(2,3)4)8-12-6-7-13-14(9-12)20-10-19-13/h6-7,9,11H,8,10H2,1-5H3
  • Key:AXMVJRRNQRXHMX-UHFFFAOYSA-N

N-t-BOC-MDMA is a chemical compound which can be both a synthetic precursor to, or a prodrug of the empathogenic drug MDMA. It was first identified in Australia in 2015 as a seizure by customs, and has subsequently been found in China, the Netherlands and other European countries. Originally it was thought to be intended as a non-illegal form of MDMA which could be easily converted into the prohibited final product after importation, however one seizure by police found N-t-BOC-MDMA in the process of being pressed into pills, and experiments with simulated gastric fluid confirmed that it can be broken down to MDMA by human stomach acid. Similar N-protected compounds such as N-t-BOC-methamphetamine, N-p-tosyl-methamphetamine, N-t-BOC-ketamine, N-t-BOC-norketamine, and N-methoxycarbonyl-MDA have also been encountered by law enforcement. [1] [2] [3] [4] [5] [6] [7]

Contents

N-t-BOC-methamphetamine, N-p-tosyl-methamphetamine, N-t-BOC-ketamine, and N-methoxycarbonyl-MDA Protected-narc structure.png
N-t-BOC-methamphetamine, N-p-tosyl-methamphetamine, N-t-BOC-ketamine, and N-methoxycarbonyl-MDA

N-t-BOC-MDMA has been specifically listed as an illicit drug in Singapore and South Korea, [8] [9] but is also controlled by general drug analogue provisions in Australia and various other countries.

See also

Related Research Articles

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Club drugs, also called rave drugs or party drugs, are a loosely defined category of recreational drugs which are associated with discothèques in the 1970s and nightclubs, dance clubs, electronic dance music (EDM) parties, and raves in the 1980s to today. Unlike many other categories, such as opiates and benzodiazepines, which are established according to pharmaceutical or chemical properties, club drugs are a "category of convenience", in which drugs are included due to the locations they are consumed and/or where the user goes while under the influence of the drugs. Club drugs are generally used by adolescents and young adults.

<span class="mw-page-title-main">Clandestine chemistry</span> Illegal preparation of chemicals

Clandestine chemistry is chemistry carried out in secret, and particularly in illegal drug laboratories. Larger labs are usually run by gangs or organized crime intending to produce for distribution on the black market. Smaller labs can be run by individual chemists working clandestinely in order to synthesize smaller amounts of controlled substances or simply out of a hobbyist interest in chemistry, often because of the difficulty in ascertaining the purity of other, illegally synthesized drugs obtained on the black market. The term clandestine lab is generally used in any situation involving the production of illicit compounds, regardless of whether the facilities being used qualify as a true laboratory.

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

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<span class="mw-page-title-main">Nimetazepam</span> Benzodiazepine medication

Nimetazepam is an intermediate-acting hypnotic drug which is a benzodiazepine derivative. It was first synthesized by a team at Hoffmann-La Roche in 1964. It possesses powerful hypnotic, anxiolytic, sedative, and skeletal muscle relaxant properties. Nimetazepam is also a particularly potent anticonvulsant. It is marketed in 5 mg tablets known as Erimin, which is the brand name manufactured and marketed by the large Japanese corporation Sumitomo. Japan is the sole manufacturer of nimetazepam in the world. Outside of Japan, Erimin is available in much of East and Southeast Asia and was widely prescribed for the short-term treatment of severe insomnia in patients who have difficulty falling asleep or maintaining sleep. Sumitomo has ceased manufacturing Erimin since November 2015. It is still available as a generic drug or as Lavol.

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MDAI (5,6-methylenedioxy-2-aminoindane) is a drug developed in the 1990s by a team led by David E. Nichols at Purdue University. It acts as a non-neurotoxic and highly selective serotonin releasing agent (SSRA) in vitro and produces entactogen effects in humans.

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

5F-ADB (also known as MDMB-5F-PINACA and 5F-MDMB-PINACA) is an indazole-based synthetic cannabinoid from the indazole-3-carboxamide family, which has been used as an active ingredient in synthetic cannabis products and has been sold online as a designer drug. 5F-ADB is a potent agonist of the CB1 receptor, though it is unclear whether it is selective for this target. 5F-ADB was first identified in November 2014 from post-mortem samples taken from an individual who had died after using a product containing this substance. Subsequent testing identified 5F-ADB to have been present in a total of ten people who had died from unexplained drug overdoses in Japan between September 2014 and December 2014. 5F-ADB is believed to be extremely potent based on the very low levels detected in tissue samples, and appears to be significantly more toxic than earlier synthetic cannabinoid drugs that had previously been sold.

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

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

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<span class="mw-page-title-main">Substituted phenylmorpholine</span> Class of chemical compounds

Substituted phenylmorpholines, or substituted phenmetrazines alternatively, are chemical derivatives of phenylmorpholine or of the psychostimulant drug phenmetrazine. Most such compounds act as releasers of monoamine neurotransmitters, and have stimulant effects. Some also act as agonists at serotonin receptors, and compounds with an N-propyl substitution act as dopamine receptor agonists. A number of derivatives from this class have been investigated for medical applications, such as for use as anorectics or medications for the treatment of ADHD. Some compounds have also become subject to illicit use as designer drugs.

<span class="mw-page-title-main">6-Chloro-MDMA</span> MDMA derivative drug

6-Chloro-MDMA is a derivative of the amphetamine drug MDMA, which has been identified both in seized "ecstasy" tablets and in urine samples from drug users. It is thought most likely to be an impurity from synthesis and its pharmacological properties have not been established; however, it has been banned in several countries.

<span class="mw-page-title-main">Substituted benzofuran</span> Class of chemical compounds

The substituted benzofurans are a class of chemical compounds based on the heterocyclyc and polycyclic compound benzofuran. Many medicines use the benzofuran core as a scaffold, but most commonly the term is used to refer to the simpler compounds in this class which include numerous psychoactive drugs, including stimulants, psychedelics and empathogens. In general, these compounds have a benzofuran core to which a 2-aminoethyl group is attached, and combined with a range of other substituents. Some psychoactive derivatives from this family have been sold under the name Benzofury.

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MDMB-5Br-INACA is an indazole-3-carboxamide derivative which has been sold as a designer drug. Surprisingly it appears to produce psychoactive activity despite the lack of a "tail" group at the indazole 1-position, but is of relatively low potency and has been encountered being misrepresented as other illicit drugs such as MDMA.

<span class="mw-page-title-main">1-Boc-4-AP</span> Chemical compound

1-Boc-4-AP is a compound used as an intermediate in the manufacture of fentanyl, as well as various related derivatives such as butyrylfentanyl, furanylfentanyl, benzylfentanyl and homofentanyl, among others. It is an N-protected derivative of 4-anilinopiperidine which can be readily converted to fentanyl or related analogues in several straightforward synthetic steps. It was classified as a DEA List 1 Chemical in 2022, and is also controlled in various other jurisdictions. Its possession, sale and importation are consequently heavily regulated throughout much of the world. 1-Boc-4-AP has also been identified as an impurity in other designer drug products, though it is unclear if it has any pharmacological activity in its own right.

References

  1. Collins M, Donnelly C, Cameron S, Tahtouh M, Salouros H (March 2017). "Identification and characterization of N-tert-butoxycarbonyl-MDMA: a new MDMA precursor". Drug Testing and Analysis. 9 (3): 399–404. doi:10.1002/dta.2059. PMID   27574107.
  2. Sugie KI, Kurakami D, Akutsu M, Saito K (2018). "Rapid detection of tert-butoxycarbonyl-methamphetamine by direct analysis in real time time-of-flight mass spectrometry". Forensic Toxicology. 36 (2): 261–269. doi:10.1007/s11419-017-0400-y. PMC   6002434 . PMID   29963202.
  3. Salouros H (2018). "Illicit drug chemical profiling: current and future state". Australian Journal of Forensic Sciences. 50 (6): 689–696. doi:10.1080/00450618.2018.1424244. S2CID   80559699.
  4. Collins M, Bhattarai A, Salouros H (2018). "Another chemically masked drug: p-tosyl methylamphetamine". Drug Testing and Analysis. 10 (5): 898–905. doi:10.1002/dta.2363. PMID   29388381.
  5. Johnson CS, Bogun B (2019). "Chemical camouflage: illicit drug concealment using di-tert-butyldicarbonate". Australian Journal of Forensic Sciences. 51: S217–S219. doi:10.1080/00450618.2019.1569135. S2CID   86747489.
  6. European Monitoring Centre for Drugs and Drug Addiction (2019). "Drug precursor developments in the European Union" (PDF). EMCDDA Papers. Luxembourg: Publications Office of the European Union.
  7. "Prosecutors Detail 500 Kilogram Ketamine Precursor Raid". ICRT.com. 3 March 2020.
  8. "Singapore Misuse of Drugs (Amendment No. 2) Regulations 2020".
  9. "Han-soo L. Ministry lists 10 substances on temporary narcotics list". Korea Biomedical Review. 11 May 2018.