4-bromo-2,5-dimethoxyphenylethylamine

from Wikipedia, the free encyclopedia
Structural formula
Structure of 2C-B
General
Surname 4-bromo-2,5-dimethoxyphenylethylamine
other names
  • 2C-B
  • 4-bromo-2,5-dimethoxyphenethyl-azane
  • 2- (4-Bromo-2,5-dimethoxyphenyl) ethanamine
Molecular formula C 10 H 14 BrNO 2
Brief description

white solid (hydrochloride)

External identifiers / databases
CAS number 66142-81-2
EC number 636-275-4
ECHA InfoCard 100.164.088
PubChem 98527
ChemSpider 88978
DrugBank DB01537
Wikidata Q229942
properties
Molar mass 260.1 g mol −1
Physical state

firmly

Melting point

234–235 ° C (hydrochloride)

safety instructions
GHS labeling of hazardous substances

Hydrochloride

06 - Toxic or very toxic

danger

H and P phrases H: 300-310-330
P: 260-264-280-284-301 + 310-302 + 350
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

2C-B pill

The chemical substance 4-bromo-2,5-dimethoxyphenylethylamine (also abbreviated to 2C-B ) structurally belongs to the group of phenylethylamines as well as to the group of "2C" compounds . It is also known by the following names: Bromo , Erox , Nexus , Venus, and Ubulawu Nomathotholo . 2C-B is the most common admixture with other drugs belonging to the group of new psychoactive substances in the EU .

history

In 1974 Alexander Shulgin synthesized 2C-B for the first time, and the corresponding publication appeared a year later.

synthesis

Numerous synthetic routes are known. A possible one is described in PIHKAL . 2,5-Dimethoxybenzaldehyde is used as the base material , which reacts with nitromethane to form the corresponding nitrostyrene, which is then reduced to 2,5-dimethoxyphenylethylamine (2C-H) using LAH . This is then brominated with elemental bromine to form 2C-B .

Synthesis of 2C-B

Analytics

2C-B can be detected in urine by HPLC , LC-MS or GC-MS .

Pharmacological properties

Mechanism of action

2C-B is a psychoactive analog of mescaline . It binds to serotonin receptors and thus changes the flow of excitation transmission in the brain. Serotonin is a neurotransmitter that is largely responsible for a person's mood. Among other things, 2C-B acts as a partial agonist of the serotonin receptors 5-HT 2A / 2C .

metabolism

2C-B is degraded to 2-4-bromo-2,5-dimethoxyphenyl-ethanol (BDMPE) by oxidative deamination .

Legal status

Since March 2001, 2C-B has been listed by the UN's Narcotics Control Council in Schedule II of the Convention on Psychotropic Substances and is therefore theoretically illegal worldwide.

In Germany, the substance is subject to the Narcotics Act . It is a non- marketable narcotic of Annex I.

In the USA , 2C-B was included in Schedule I of the Controlled Substances Act on January 6, 1994 by the DEA through an urgent procedure - substances with a high potential for abuse and no proven medical benefit correspond to this class. Since then, it has been illegal to own or sell 2C-B in the US. Since June 2, 1995 it has been permanent in CSA Schedule I, Section (d). 2C-B was misspelled in the 26th edition of the Green List in 2015, 2 CB. It was corrected in the following Green List 27th edition, 2016 . 2C-B was declared illegal in the Netherlands on July 9, 1997, and in Japan in June 1998 (before that, it was available under the trade name Performax ). It is also illegal in Belgium. In the Czech Republic , possession of more than 200 mg can be punished with a two-year prison term. In Denmark it is a category B drug. In Estonia it is on Schedule I, and in Italy as well (Tabella I). In Norway it was added to Schedule II on March 22, 2004. In Poland it is in Appendix I (IP group). In Spain , it was included in Category II prohibited substances in 2002. In Sweden it is in Appendix I., since April 1, 1999 ( SFS 1999: 58 ) and LVFS 2002: 4 from 2002. There, 2C-B was incorrectly described as 2-CB , the correction was made in LVFS 2009: 22 in 2009. In Switzerland it is in Appendix D of the DetMV . In the UK, all drugs under the Drugs Controlled by the UK Misuse of Drugs Act are class A 2C family drugs . In Argentina it is on list 1, as is 2C-I or 2C-T-2 . It is a banned substance in Brazil . In Australia , 2C-B is in Appendix B. In Canada , it falls under CDSA Schedule III as 4-Bromo-2,5-dimethoxybenzeneethanamine and any salt, isomer or salt of isomer thereof .

See also

literature

Individual evidence

  1. a b c d data sheet (±) -1- (4-Bromo-2,5-dimethoxyphenyl) -2-ethanamine hydrochloride from Sigma-Aldrich , accessed on May 12, 2017 ( PDF ).
  2. ^ CV Giné, IF Espinosa, MV Vilamala: New psychoactive substances as adulterants of controlled drugs. A worrying phenomenon? In: Drug testing and analysis. Volume 6, number 7-8, Jul-Aug 2014, pp. 819-824, doi: 10.1002 / dta.1610 . PMID 24470121 .
  3. ^ AT Shulgin, MF Carter: Centrally Active Phenethylamines. In: Psychopharmacology Communications. 1 (1), 1975, pp. 93-98, PDF (accessed February 12, 2018).
  4. G. Appendino, A. Minassi, O. Taglialatela-Scafati: Recreational drug discovery: natural products as lead structures for the synthesis of smart drugs. In: Natural product reports. Volume 31, Number 7, July 2014, pp. 880-904, doi: 10.1039 / c4np00010b . PMID 24823967 (Review) ( free full text ).
  5. Alexander Shulgin: Pihkal. Transform Press, 1995, ISBN 0-9630096-0-5 .
  6. M. Williams, J. Martin, P. Galettis: A Validated Method for the Detection of 32 Bath Salts in Oral Fluid. In: Journal of analytical toxicology. Volume 41, Number 8, October 2017, pp. 659-669, doi: 10.1093 / jat / bkx055 . PMID 28985394 .
  7. S. Kerrigan, A. Mott, B. Jatzlau, F. Ortiz, L. Perrella, S. Martin, K. Bryand: Designer psychostimulants in urine by liquid chromatography-tandem mass spectrometry. In: Journal of forensic sciences. Volume 59, number 1, January 2014, pp. 175-183, doi: 10.1111 / 1556-4029.12306 . PMID 24313279 .
  8. T. Kanamori, K. Nagasawa, K. Kuwayama, K. Tsujikawa, YT Iwata, H. Inoue: Analysis of 4-bromo-2,5-dimethoxyphenethylamine abuser's urine: identification and quantitation of urinary metabolites. In: Journal of forensic sciences. Volume 58, number 1, January 2013, pp. 279-287, doi: 10.1111 / j.1556-4029.2012.02289.x . PMID 23066942 .
  9. F. Caudevilla-Gálligo, J. Riba, M. Ventura, D. González, M. Farré, MJ Barbanoj, JC Bouso: 4-Bromo-2,5-dimethoxyphenethylamine (2C-B): presence in the recreational drug market in Spain, pattern of use and subjective effects. In: Journal of psychopharmacology. Volume 26, Number 7, July 2012, pp. 1026-1035, doi: 10.1177 / 0269881111431752 . PMID 22234927 .
  10. JJ Nugteren-van Lonkhuyzen, AJ van Riel, TM Brunt, L. Hondebrink: Pharmacokinetics, pharmacodynamics and toxicology of new psychoactive substances (NPS): 2C-B, 4-fluoroamphetamine and benzofurans. In: Drug and alcohol dependence. Volume 157, December 2015, pp. 18-27, doi: 10.1016 / j.drugalcdep.2015.10.011 . PMID 26530501 (Review).
  11. AL Halberstadt: Pharmacology and Toxicology of N-Benzylphenethylamine ("NBOMe") Hallucinogens. In: Current topics in behavioral neurosciences. Volume 32, 2017, pp. 283-311, doi : 10.1007 / 7854_2016_64 . PMID 28097528 (Review).
  12. H. Carmo, JG Hengstler, D. de Boer, M. Ringel, F. Remião, F. Carvalho, E. Fernandes, LA dos Reys, F. Oesch, M. de Lourdes Bastos: Metabolic pathways of 4-bromo- 2,5-dimethoxyphenethylamine 2C-B: analysis of phase I metabolism with hepatocytes of six species including human. In: Toxicology. Volume 206, Issue 1, 2005, pp. 75-89. doi: 10.1016 / j.tox.2004.07.004 .
  13. Law on the traffic in narcotics (Narcotics Act - BtMG) - Annex I (to Section 1, Paragraph 1) - (Narcotics that are not marketable). In: Federal Law Gazette. Accessed on January 28, 2018 .
  14. ^ List of Psychotropic Substances under International Control. (PDF) 26th edition. International Narcotics Control Boards, 2015, archived from the original on January 19, 2016 ; accessed on May 11, 2018 (English).
  15. ^ List of Psychotropic Substances under International Control. (PDF) 27th edition. International Narcotics Control Boards, 2016, archived from the original on April 21, 2017 ; accessed on May 11, 2018 (English).
  16. Bekendtgørelse om euforiserende materials. July 1, 2008, accessed October 1, 2013 (Danish).
  17. Italy Drug Schedule (Tabella I). (No longer available online.) Archived from the original on June 27, 2011 ; accessed on December 5, 2018 .
  18. ^ Norway Drug Schedule. Retrieved December 5, 2018 .
  19. Förordning (1999: 58) om förbud mot vissa hälsofarliga varo. February 25, 1999, accessed October 1, 2013 (Swedish).
  20. Föreskrifter om ändring i Läkemedelsverkets föreskrifter (LVFS 1997: 12) om förteckningar över narcotics: LVFS 2002: 4. (PDF) Retrieved December 5, 2018 (Swedish).
  21. Föreskrifter om ändring i Läkemedelsverkets föreskrifter (LVFS 1997: 12) om förteckningar över narcotics: LVFS 2009: 22. (PDF) Retrieved December 5, 2018 (Swedish).
  22. List of all substances containing narcotics. (PDF) (No longer available online.) Swissmedic, Swiss Agency for Therapeutic Products, August 18, 2011, p. 2 , archived from the original on March 15, 2012 ; Retrieved November 30, 2013 .
  23. BBC - Advice - 2CB. BBC , accessed October 1, 2013 .
  24. ^ Last Argentina Controlled Drugs List. (PDF) Retrieved May 15, 2012 .
  25. CDSA Schedule II. Accessed December 5, 2018 .