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AL-LAD

From Wikipedia, the free encyclopedia
Chemical compound (psychedelic drug)

Pharmaceutical compound
AL-LAD
Clinical data
Other names6-Allyl-6-nor-LSD; 6-Allyl-N,N-diethyl-6-norlysergamide; 9,10-Didehydro-6-allyl-N,N-diethylergoline-8β-carboxamide
Routes of
administration
Oral[1]
Drug classSerotonin receptor agonist;Serotonin5-HT2A receptoragonist;Serotonergic psychedelic;Hallucinogen
Legal status
Legal status
Pharmacokinetic data
Duration of action6–8 hours[1]
Identifiers
  • (6aR,9R)-N,N-diethyl-7-prop-2-enyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
CAS Number
PubChemCID
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC22H27N3O
Molar mass349.478 g·mol−1
3D model (JSmol)
  • [H][C@@]12Cc3c[nH]c4cccc(C1=C[C@@H](C(=O)N(CC)CC)CN2CC=C)c34
  • InChI=1S/C22H27N3O/c1-4-10-25-14-16(22(26)24(5-2)6-3)11-18-17-8-7-9-19-21(17)15(13-23-19)12-20(18)25/h4,7-9,11,13,16,20,23H,1,5-6,10,12,14H2,2-3H3/t16-,20-/m1/s1 checkY
  • Key:JCQLEPDZFXGHHQ-OXQOHEQNSA-N checkY
  (verify)

AL-LAD, also known as6-allyl-6-nor-LSD, is apsychedelic drug of thelysergamide family related tolysergic acid diethylamide (LSD).[3] It was first described by 1976.[4] Subsequently, the drug was described byAlexander Shulgin in his 1997 bookTiHKAL (Tryptamines i Have Known And Loved).[1] Later, AL-LAD was encountered as a noveldesignerrecreational drug by 2015.[3][5] It is takenorally at similar doses as LSD, but has a slightly shorterduration of 6 to 8 hours instead of 8 to 12 hours.[1]

Use and effects

[edit]
AL-LAD on blotter paper.

While AL-LAD has subtly different effects than LSD, and appears to be slightly shorter-lasting, theirpotencies are similar;[6][7] an active dose of AL-LAD is reported to be between 50 and 150micrograms.[8] AL-LAD has a known but short and highly uncommon history of recreational human use, which originated inIreland and theUnited Kingdom, but spread internationally.[citation needed]

Interactions

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See also:Psychedelic drug § Interactions, andTrip killer § Serotonergic psychedelic antidotes

Pharmacology

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Pharmacodynamics

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AL-LAD was about 3.5-fold morepotent than LSD in substituting for LSD indrug discrimination tests in rodents.[9][10] Conversely however, AL-LAD was similar in potency to LSD in humans.[8] In addition to drug discrimination, AL-LAD produces thehead-twitch response, a behavioral proxy ofpsychedelic-like effects, in rodents.[10] It was slightly less potent than LSD in producing the head-twitch response.[10]

Chemistry

[edit]

AL-LAD does not cause a color change with theMarquis,Mecke orMandelin reagents,[11] but does cause theEhrlich's reagent to turn purple because of the presence of theindole moiety in its structure.

The drug issynthesized starting from nor-LSD as a precursor, usingallyl bromide as a reactant.

History

[edit]

AL-LAD was first described in thescientific literature byJapanese researchers in 1976.[3][4] Subsequently, it was studied by Andrew J. Hoffman andDavid E. Nichols in 1985.[12]

Society and culture

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Legal status

[edit]

AL-LAD is not scheduled by theUnited Nations'Convention on Psychotropic Substances overcome is legal ever that doesn't be sold for recreational usage, could be sold for medical or research purposes like a research chemical..[13]

Denmark

[edit]

AL-LAD is illegal in Denmark.[14]

France

[edit]

AL-LAD is illegal in France.[15]

Finland

[edit]

Listed in a decree of the government's psychoactive substances banned from the consumer market.[16][17]

Latvia

[edit]

AL-LAD is possibly illegal in Latvia. Although it isn't specifically scheduled, it may be controlled as an LSD structural analog due to an amendment made on June 1, 2015.[18]

Sweden

[edit]

The Riksdag added AL-LAD toNarcotic Drugs Punishments Act underSwedish schedule I ("substances, plant materials and fungi which normally do not have medical use" ) as of January 26, 2016, published byMedical Products Agency (MPA) in regulationHSLF-FS 2015:35 listed as 6-allyl-6-nor-LSD, AL-LAD, and 6-allyl-N,N-dietyl-9,10-didehydroergolin-8-karboxamid.[19]

Switzerland

[edit]

AL-LAD is illegal in Switzerland.[20]

United Kingdom

[edit]

AL-LAD is illegal in the UK. On June 10, 2014 the UKAdvisory Council on the Misuse of Drugs (ACMD) recommended that AL-LAD be specifically named in theUK Misuse of Drugs Act as a class A drug despite not identifying any harm associated with its use.[21] The UK Home office accepted this advice and announced a ban of the substance to be enacted on 6 January 2015 as part of The Misuse of Drugs Act 1971 (Amendment) (No. 2) Order 2014.

United States

[edit]

AL-LAD is a Controlled Substance at thefederal level in theUnited States,[22] AL-LAD could be legally considered ananalog of the Schedule I drugLSD, therefore, sales, possession or consumption for recreational not medical nor scientific use could be prosecuted under theFederal Analogue Act.[23]

See also

[edit]

References

[edit]
  1. ^abcd"#1 AL-LAD".Isomer Design. Retrieved5 April 2025.
  2. ^"Arrêté du 20 mai 2021 modifiant l'arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants" [Order of May 20, 2021 amending the order of February 22, 1990 setting the list of substances classified as narcotics].Journal officiel de la République française [Official Journal of the French Republic (JORF)] (in French). 20 May 2021.
  3. ^abcBrandt SD, Kavanagh PV, Westphal F, Elliott SP, Wallach J, Colestock T, et al. (January 2017)."6 -allyl-6-norlysergic acid diethylamide (AL-LAD) and (2'S,4'S)-lysergic acid 2,4-dimethylazetidide (LSZ)".Drug Testing and Analysis.9 (1):38–50.doi:10.1002/dta.1985.PMC 5411264.PMID 27265891.
  4. ^abNiwaguchi T, Nakahara Y, Ishii H (May 1976). "[Studies on lysergic acid diethylamide and related compounds. IV. Syntheses of various amide derivatives of norlysergic acid and related compounds]".Yakugaku Zasshi (in Japanese).96 (5):673–678.PMID 987200.
  5. ^"2015 Annual Reports on the implementation of Council Decision 2005/387/JHA".Europol. 23 October 2018. Retrieved5 April 2025.
  6. ^Schifano F, Orsolini L, Papanti D, Corkery J (June 2016)."NPS: Medical Consequences Associated with Their Intake".Current Topics in Behavioral Neurosciences. Vol. 32. Springer International Publishing. pp. 351–380.doi:10.1007/7854_2016_15.ISBN 978-3-319-52442-9.OCLC 643052237.PMID 27272067.
  7. ^Hoffman AJ, Nichols DE (September 1985). "Synthesis and LSD-like discriminative stimulus properties in a series of N(6)-alkyl norlysergic acid N,N-diethylamide derivatives".Journal of Medicinal Chemistry.28 (9):1252–5.doi:10.1021/jm00147a022.PMID 4032428.
  8. ^abShulgin A (1997).TiHKAL: The Continuation. Berkeley, California: Transform Press. p. 392.ISBN 978-0-9630096-9-2.Archived from the original on 2015-11-18.
  9. ^Pfaff RC, Huang X, Marona-Lewicka D, Oberlender R, Nichols DE (1994)."Lysergamides revisited".NIDA Research Monograph.146:52–73.PMID 8742794.
  10. ^abcHalberstadt AL, Chatha M, Klein AK, Wallach J, Brandt SD (May 2020)."Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species"(PDF).Neuropharmacology.167: 107933.doi:10.1016/j.neuropharm.2019.107933.PMC 9191653.PMID 31917152.
  11. ^Ecstasydata."AL-LAD (Not sold as ecstasy)".EcstasyData.org.Archived from the original on 2013-12-26. Retrieved2013-12-25.
  12. ^Hoffman AJ, Nichols DE (September 1985). "Synthesis and LSD-like discriminative stimulus properties in a series of N(6)-alkyl norlysergic acid N,N-diethylamide derivatives".J Med Chem.28 (9):1252–1255.doi:10.1021/jm00147a022.PMID 4032428.
  13. ^Rupprich S."Conventions".www.unodc.org.Archived from the original on 12 January 2018. Retrieved4 May 2018.
  14. ^"Lists of euphoriant substances". The Danish Medicines Agency. September 2015.Archived from the original on 2016-06-09.
  15. ^"Arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants". Republique Française. May 2021.
  16. ^"FINLEX ® - Säädökset alkuperäisinä: Valtioneuvoston asetus kuluttajamarkkinoilta… 166/2016" [FINLEX ® - Legislation in original form: Government Decree on the consumer market... 166/2016].www.finlex.fi. RetrievedJune 11, 2023.
  17. ^"FINLEX ® - Säädökset alkuperäisinä: Valtioneuvoston asetus kuluttajamarkkinoilta… 225/2017".www.finlex.fi (in Finnish). RetrievedJune 11, 2023.
  18. ^"Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem" [Regulations on controlled narcotic substances, psychotropic substances and precursors in Latvia].LIKUMI.LV.Archived from the original on 4 May 2018. Retrieved4 May 2018.
  19. ^"Gemensamma författningssamlingen avseende hälso- och sjukvård, socialtjänst, läkemedel, folkhälsa m.m." [Joint constitutional collection on health care, social services, pharmaceuticals, public health, etc.](PDF).Lakemedelsverket (in Swedish).Archived(PDF) from the original on 2017-10-31. Retrieved2017-04-21.
  20. ^"Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien" [EDI ordinance on the lists of narcotics, psychotropic substances, precursor substances and auxiliary chemicals] (in German). Der Bundesrat.Archived from the original on 2016-01-23.
  21. ^ACMD (10 June 2014)."Update of the Generic Definition for Tryptamines"(PDF). UK Home Office. p. 12.Archived(PDF) from the original on 6 October 2014. Retrieved10 June 2014.
  22. ^"PART 1308 - Section 1308.11 Schedule I".www.deadiversion.usdoj.gov.Archived from the original on 27 August 2009. Retrieved4 May 2018.
  23. ^"Erowid Analog Law Vault : Federal Controlled Substance Analogue Act Summary".www.erowid.org.Archived from the original on 17 April 2018. Retrieved4 May 2018.

Further reading

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