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Description

Butylone Also known as:

  • 1-(1,3-Benzodioxol-5-yl)-2-(methylamino)-1-butanon[German][ACD/IUPAC Name]
  • 1-(1,3-Benzodioxol-5-yl)-2-(methylamino)-1-butanone[ACD/IUPAC Name]
  • 1-(1,3-Benzodioxol-5-yl)-2-(méthylamino)-1-butanone[French][ACD/IUPAC Name]
  • 1-Butanone, 1-(1,3-benzodioxol-5-yl)-2-(methylamino)-[ACD/Index Name]
  • 2-methylamino-1-(3,4-methylenedioxyphenyl)butan-1-one
  • 2-methylamino-1-(3,4-methylenedioxyphenyl)-butan-1-one
  • bk-MBDB
  • UNII:X72T4EQ4FQ
  • X72T4EQ4FQ
  • β-keto-N-methylbenzodioxolylbutanamine
  • 1-(1,3-benzodioxol-5-yl)-2-(methylamino)butan-1-one
  • -(1,3-benzodioxol-5-yl)-2-(methylamine)buthane-1-one[ACD/IUPAC Name]
  • 1-(benzo[d][1,3]dioxol-5-yl)-2-(methylamino)butan-1-one

Empathogen and stimulant of the cathinone class.

Summary

It is the β-keto analog of MBDB and the substituted methylenedioxy analogue of buphedrone. As a designer drug, it is commonly sold on the street along with ethylone as a substitute or counterfeit for MDMA and methylone (all of which have collectively come to be referred to as "Molly") due to methylone's declining availability on the research chemical market. However, in spite of behavioral and pharmacological similarities between butylone and MDMA, the observed subjective effects of both substances are not completely identical.

Subjective effects include stimulation, thought acceleration, motivation enhancement, increased libido, appetite suppression, and euphoria, Butylone is reported to be less potent than its relatives methylone and ethylone as well as possessing more classic stimulant as opposed to entactogenic effects. Butylone has a very short history of human use and very little data exists about its pharmacological properties, metabolism, and toxicity. It is highly advised to use harm reduction practices if using this substance.

Chemistry

Cathinones are structurally similar to amphetamines in that they contain a phenethylamine core featuring a phenyl ring bound to an amino (NH2) group through an ethyl chain with an additional ethyl substitution at Rα.

Cathinones such as butylone are alpha-methylated phenethylamines (i.e.

amphetamines) but differ from them with the addition of a ketone functional group (a carbonyl group at Rβ).

Butylone contains a methyl substitution at RN, a substitution which is shared with MDEA, ethylone, 4-MEC, and certain other stimulants and entactogens.

Additionally, butylone contains substitutions at R3 and R4 of the phenyl ring with oxygen groups.

These oxygen groups are incorporated into a methylenedioxy ring through a methylene chain.

Butylone shares this methylenedioxy ring with MDA, MDAI and MDMA.

Common NameButylone
Systematic nameButylone
FormulaC_{12}H_{15}NO_{3}
SMILESCCC(C(=O)c1ccc2c(c1)OCO2)NC
Std. InChiInChI=1S/C12H15NO3/c1-3-9(13-2)12(14)8-4-5-10-11(6-8)16-7-15-10/h4-6,9,13H,3,7H2,1-2H3
Std. InChiKeyCGKQZIULZRXRRJ-UHFFFAOYSA-N
Avg. Mass221.2524 Da
Molecular Weight221.2524
Monoisotopic Mass221.105194 Da
Nominal Mass221
ChemSpider ID21106270

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Dose Chart

Oral
Threshold20-40mg
Light40-70mg
Common70-100mg
Strong150-200mg
Heavy200mg+

Duration Chart

Butylone Duration Data
Onset25-45 minutes
Duration3-5 hours
After-effects2-12 hours

Interactions

Caution

  1. Mushrooms
    • Stimulants increase anxiety levels and the risk of thought loops which can lead to negative experiences
  2. LSD
    • Stimulants increase anxiety levels and the risk of thought loops which can lead to negative experiences
  3. DMT
    • Stimulants increase anxiety levels and the risk of thought loops which can lead to negative experiences
  4. Mescaline
    • The focus and anxiety caused by stimulants is magnified by psychedelics and results in an increased risk of thought loops
  5. 2C-x
    • The anxiogenic and focusing effects of stimulants increase the chance of unpleasant thought loops. The combination is generally uneccessary because of the stimulating effects of psychedelics. Combination of the stimulating effects may be uncomfortable.
  6. Cannabis
    • Stimulants increase anxiety levels and the risk of thought loops which can lead to negative experiences
  7. Ketamine
    • No unexpected interactions, though likely to increase blood pressure but not an issue with sensible doses. Moving around on high doses of this combination may be ill advised due to risk of physical injury.
  8. MXE
    • Risk of tachycardia, hypertension, and manic states
  9. Cocaine
    • This combination of stimulants will increase strain on the heart. It is not generally worth it as cocaine has a mild blocking effect on dopamine releasers like amphetamine
  10. Caffeine
    • This combination of stimulants is not generally necessary and may increase strain on the heart, as well as potentially causing anxiety and greater physical discomfort.
  11. Alcohol
    • Drinking on stimulants is risky because the sedative effects of the alcohol are reduced, and these are what the body uses to gauge drunkenness. This typically leads to excessive drinking with greatly reduced inhibitions, high risk of liver damage and increased dehydration. They will also allow you to drink past a point where you might normally pass out, increasing the risk. If you do decide to do this then you should set a limit of how much you will drink each hour and stick to it, bearing in mind that you will feel the alcohol and the stimulant less. Extended release formulations may severely impede sleep, further worsening the hangover.
  12. GHB/GBL
    • Stimulants increase respiration rate allowing a higher dose of sedatives. If the stimulant wears off first then the opiate may overcome the patient and cause respiratory arrest.
  13. Opioids
    • Stimulants increase respiration rate allowing a higher dose of opiates. If the stimulant wears off first then the opiate may overcome the patient and cause respiratory arrest.

Dangerous

  1. DOx
    • The combined stimulating effects of the two can lead to an uncomfortable body-load, while the focusing effects of amphetamine can easily lead to thought loops. Coming down from amphetamines while the DOx is still active can be quite anxiogenic.
  2. NBOMes
    • Amphetamines and NBOMes both provide considerable stimulation. When combined they can result in tachycardia, hypertension, vasoconstriction and in extreme cases heart failure. The anxiogenic and focusing effects of stimulants are also not good in combination with psychedelics as they can lead to unpleasant thought loops. NBOMes are known to cause seizures and stimulants can increase this risk.
  3. 2C-T-x
    • Stimulants increase anxiety levels and the risk of thought loops which can lead to negative experiences. In extreme cases, they can result in severe vasoconstriction, tachycardia, hypertension, and in extreme cases heart failure.
  4. 5-MeO-xxT
    • The anxiogenic and focusing effects of stimulants increase the chance of unpleasant thought loops. The combination is generally unnecessary because of the stimulating effects of psychedelics.
  5. DXM
    • Both substances raise heart rate, in extreme cases, panic attacks caused by these drugs have led to more serious heart issues.
  6. PCP
    • This combination can easily lead to hypermanic states

Low Synergy

  1. Benzodiazepines
    • Both can dull each other's effects, so if one wears off before the other it's possible to overdose due to the lack of counteraction

No Synergy

  1. SSRIs

High Synergy

  1. N2O
  2. MDMA
    • Amphetamines increase the neurotoxic effects of MDMA

Legal Status

  • Austria: Butylone is illegal to possess, produce and sell under the NPSG (New Psychoactive Substances Act).
  • Brazil: As of September 7, 2018, all cathinone analogues are controlled substances considered illegal to possess, use and distribute. This was made possible due to a blanket ban law appended to Portaria SVS/MS nº 344.
  • Canada: Butylone is controlled as a Schedule I substance.
  • China: As of October 2015 butylone is a controlled substance in China.
  • Finland: Butylone is a controlled substance.
  • Germany: Butylone is controlled under Anlage II BtMG (Narcotics Act, Schedule II) as of July 26, 2012. It is illegal to manufacture, possess, import, export, buy, sell, procure or dispense it without a license.
  • Israel: Butylone is a controlled substance.
  • Japan: Butylone is a controlled substance.
  • Norway: Butylone is a controlled substance.
  • Poland: Butylone is a controlled substance.
  • Sweden: Butylone is a Schedule I controlled substance as of February 1, 2010.
  • United Kingdom: Butylone is a Class B drug in the United Kingdom as a result of the cathinone catch-all clause.
  • United States: Butylone is unscheduled in the United States. However it could be considered an analog of methylone or MDMA, thus making it illegal under the scope of the Federal Analog Act.
  • Sources

    References

    1. "Cathinone | Ask Dr. Shulgin Online".
    2. Inhibition of plasma membrane monoamine transporters by beta-ketoamphetamines (PubMed.gov / NCBI) | http://www.ncbi.nlm.nih.gov/pubmed/10528135
    3. The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain (ScienceDirect) | http://www.sciencedirect.com/science/article/pii/S0014299906013811
    4. "Pharmacological characterization of designer cathinones in vitro" | http://onlinelibrary.wiley.com/doi/10.1111/j.1476-5381.2012.02145.x/pdf
    5. The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain (ScienceDirect) | http://www.sciencedirect.com/science/article/pii/S0014299906013811
    6. "Pharmacological characterization of designer cathinones in vitro" | http://onlinelibrary.wiley.com/doi/10.1111/j.1476-5381.2012.02145.x/pdf
    7. Treatment for amphetamine psychosis | [1]
    8. Treatment for amphetamine psychosis | [2]
    9. Hofmann FG (1983). A Handbook on Drug and Alcohol Abuse: The Biomedical Aspects (2nd ed.). New York: Oxford University Press. p. 329. ISBN 9780195030570.
    10. Treatment for amphetamine psychosis | [3]
    11. Stimulant Misuse: Strategies to Manage a Growing Problem | http://www.acha.org/prof_dev/ADHD_docs/ADHD_PDprogram_Article2.pdf
    12. http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021303s026lbl.pdf
    13. Talaie, H., Panahandeh, R., Fayaznouri, M. R., Asadi, Z., & Abdollahi, M. (2009). Dose-independent occurrence of seizure with tramadol. Journal of Medical Toxicology, 5(2), 63-67. https://doi.org/10.1007/BF03161089
    14. Gillman, P. K. (2005). Monoamine oxidase inhibitors, opioid analgesics and serotonin toxicity. British Journal of Anaesthesia, 95(4), 434-441. https://doi.org/10.1093/bja/aei210
    15. New blanket ban on synthetic illegal drugs is approved (Portuguese) | http://portal.anvisa.gov.br/noticias/-/asset_publisher/FXrpx9qY7FbU/content/combate-a-drogas-ilicitas-sinteticas-fica-mais-facil/219201/pop_up?_101_INSTANCE_FXrpx9qY7FbU_viewMode=print&_101_INSTANCE_FXrpx9qY7FbU_languageId=pt_BR
    16. "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Retrieved 1 October 2015.
    17. "Anlage II BtMG" (in German). Bundesministerium der Justiz und für Verbraucherschutz. Retrieved December 25, 2019.
    18. "Sechsundzwanzigste Verordnung zur Änderung betäubungsmittelrechtlicher Vorschriften" (in German). Bundesanzeiger Verlag. Retrieved December 25, 2019.
    19. "§ 29 BtMG" (in German). Bundesministerium der Justiz und für Verbraucherschutz. Retrieved December 25, 2019.
    20. "Föreskrifter om ändring i Läkemedelsverkets föreskrifter (LVFS 1997:12) om förteckningar över narkotika" (PDF) (in Swedish). Läkemedelsverkets författningssamling. Retrieved December 25, 2019.
    21. United Kingdom. (2010). Misuse of Drugs Act 1971 (S.I. 2010/1207). London: The Stationery Office Limited. Retrieved February 9, 2018, from https://www.legislation.gov.uk/uksi/2010/1207/made

    Information made possible with:

    1. PsychonautWiki is a community-driven online encyclopedia that aims to document the field of psychonautics in a comprehensive, scientifically-grounded manner.
    2. Erowid is a non-profit educational & harm-reduction resource with 60 thousand pages of online information about psychoactive drugs
    3. PubChem National Center for Bio Informatics
    4. Chemspider is a free chemical structure database providing fast access to over 34 million structures, properties and associated information.
    5. Wikipedia

    Additional APIs were used to construct this information. Thanks to ChemSpider, NCBI, PubChem etc.

    Data is constantly updated so please check back later to see if there is any more available information on this substance.