AL-LAD

AL-LAD
Legal status
Legal status	DE: NpSG (Industrial and scientific use only) ; UK: Class A ; Illegal in Denmark, France, Sweden and Switzerland;
Identifiers
	IUPAC name (6aR,9R)-N,N-diethyl-7-prop-2-enyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide;
CAS Number	65527-61-9 ;
PubChem CID	15227511;
ChemSpider	21106248 ;
UNII	020O2SR91L;
ChEMBL	ChEMBL281787 ;
CompTox Dashboard (EPA)	DTXSID30215822 ;
Chemical and physical data
Formula	C22H27N3O
Molar mass	349.478 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES [H][C@@]12Cc3c[nH]c4cccc(C1=C[C@@H](C(=O)N(CC)CC)CN2CC=C)c34;
	InChI 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 ; Key:JCQLEPDZFXGHHQ-OXQOHEQNSA-N ;
	(what is this?)

AL-LAD, also known as 6-allyl-6-nor-LSD, is a psychedelic drug and an analog of lysergic acid diethylamide (LSD).^[2] It is described by Alexander Shulgin in the book TiHKAL (Tryptamines i Have Known And Loved). It is synthesized starting from nor-LSD as a precursor, using allyl bromide as a reactant.

Effects in humans[]

AL-LAD on blotter paper

While AL-LAD has subtly different effects than LSD, and appears to be slightly shorter lasting, their potencies are similar;^[3]^[4] an active dose of AL-LAD is reported to be between 50 and 150 micrograms.^[5] AL-LAD has a known but short and highly uncommon history of recreational human use, which originated in Ireland and the UK, but spread internationally.

Chemistry[]

AL-LAD does not cause a color change with the Marquis, Mecke or Mandelin reagents,^[6] but does cause the Ehrlich's reagent to turn purple because of the presence of the indole moiety in its structure.

Legal status[]

AL-LAD is not scheduled by the United Nations' Convention on Psychotropic Substances.^[7]

Denmark[]

AL-LAD is illegal in Denmark.^[8]

Latvia[]

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.^[9]

Romania

AL-LAD is illegal in Romania. It is not included directly in the list of controlled substances, but it is included in an analogue act

Sweden[]

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

Switzerland[]

AL-LAD is illegal in Switzerland.^[11]

United Kingdom[]

AL-LAD is illegal in the UK. On June 10, 2014 the UK Advisory Council on the Misuse of Drugs (ACMD) recommended that AL-LAD be specifically named in the UK Misuse of Drugs Act as a class A drug despite not identifying any harm associated with its use.^[12] 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[]

AL-LAD is not scheduled as a controlled substance at the federal level in the United States,^[13] but AL-LAD could legally be considered an analog of LSD, in which case, sales or possession with intent for human consumption could be prosecuted under the Federal Analogue Act.^[14]

References[]

^ "Arrêté du 20 mai 2021 modifiant l'arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants". www.legifrance.gouv.fr (in French). 20 May 2021.
^ Brandt 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.
^ Schifano F, Orsolini L, Papanti D, Corkery J (June 2016). "NPS: Medical Consequences Associated with Their Intake". Current Topics in Behavioral Neurosciences. Current Topics in Behavioral Neurosciences. 32. Springer International Publishing. pp. 351–380. doi:10.1007/7854_2016_15. ISBN 978-3-319-52442-9. OCLC 643052237. PMID 27272067.
^ 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.
^ Shulgin, Alexander (1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. p. 392. ISBN 978-0-9630096-9-2. Archived from the original on 2015-11-18.
^ Ecstasydata. "EcstasyData.org - AL-LAD (Not sold as ecstasy)". Archived from the original on 2013-12-26. Retrieved 2013-12-25.
^ simone.rupprich. "Conventions". www.unodc.org. Archived from the original on 12 January 2018. Retrieved 4 May 2018.
^ "Lists of euphoriant substances". The Danish Medicines Agency. September 2015. Archived from the original on 2016-06-09.
^ "Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem". LIKUMI.LV. Archived from the original on 4 May 2018. Retrieved 4 May 2018.
^ "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. Retrieved 2017-04-21.
^ "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien" (in German). Der Bundesrat. Archived from the original on 2016-01-23.
^ 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. Retrieved 10 June 2014.
^ "PART 1308 - Section 1308.11 Schedule I". www.deadiversion.usdoj.gov. Archived from the original on 27 August 2009. Retrieved 4 May 2018.
^ "Erowid Analog Law Vault : Federal Controlled Substance Analogue Act Summary". www.erowid.org. Archived from the original on 17 April 2018. Retrieved 4 May 2018.

External links[]

[1] "Arrêté du 20 mai 2021 modifiant l'arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants". www.legifrance.gouv.fr (in French). 20 May 2021.

[2] Brandt 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.

[3] Schifano F, Orsolini L, Papanti D, Corkery J (June 2016). "NPS: Medical Consequences Associated with Their Intake". Current Topics in Behavioral Neurosciences. Current Topics in Behavioral Neurosciences. 32. Springer International Publishing. pp. 351–380. doi:10.1007/7854_2016_15. ISBN 978-3-319-52442-9. OCLC 643052237. PMID 27272067.

[pmid4032428-4] 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.

[tihkal_26-5] Shulgin, Alexander (1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. p. 392. ISBN 978-0-9630096-9-2. Archived from the original on 2015-11-18.

[6] Ecstasydata. "EcstasyData.org - AL-LAD (Not sold as ecstasy)". Archived from the original on 2013-12-26. Retrieved 2013-12-25.

[UNCPS-7] simone.rupprich. "Conventions". www.unodc.org. Archived from the original on 12 January 2018. Retrieved 4 May 2018.

[8] "Lists of euphoriant substances". The Danish Medicines Agency. September 2015. Archived from the original on 2016-06-09.

[likumi.lv-9] "Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem". LIKUMI.LV. Archived from the original on 4 May 2018. Retrieved 4 May 2018.

[10] "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. Retrieved 2017-04-21.

[11] "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien" (in German). Der Bundesrat. Archived from the original on 2016-01-23.

[ACMD_tryptamines-12] 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. Retrieved 10 June 2014.

[PART_1308_—_SCHEDULES_OF_CONTROLLED_SUBSTANCES_-_1308.11_Schedule_I-13] "PART 1308 - Section 1308.11 Schedule I". www.deadiversion.usdoj.gov. Archived from the original on 27 August 2009. Retrieved 4 May 2018.

[14] "Erowid Analog Law Vault : Federal Controlled Substance Analogue Act Summary". www.erowid.org. Archived from the original on 17 April 2018. Retrieved 4 May 2018.

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v t Ergolines
Lysergic acid derivatives	2-Bromo-LSD (BOL-148) Amesergide Bromocriptine Cabergoline Dihydroergocornine Dihydroergocristine Dihydroergocryptine (Dihydroergonovine, Dihydroergobasine) Dihydroergotamine Epicriptine Ergine (LSA; LA-111; Lysergamide) Ergocornine Ergocristine Ergocryptine Ergoloid (Dihydroergotoxine) Ergometrine (Ergonovine, Ergobasine) Ergometrinine Ergostine Ergotamine Ergotoxine Ergovaline Lisuride LY-215,840 LSH Lysergic acid Lysergic acid methyl ester Lysergol Mesulergine Metergoline MIPLA Methysergide Sergolexole
Psychedelic lysergamides	1B-LSD 1cP-LSD 1P-ETH-LAD 1P-LSD AL-LAD ALD-52 BU-LAD Diallyllysergamide (DAL) Dimethyllysergamide (DAM-57) ECPLA Ergonovine ETFELA ETH-LAD IP-LAD LAE-32 LSD LPD-824 LSM-775 LSH LSD-Pip Lysergic Acid 2-Butylamide Lysergic Acid 2,4-Dimethylazetidide Lysergic Acid 3-Pentylamide Methylergometrine (Methylergonovine, Methylergobasine) MIPLA MLD-41 PARGY-LAD PRO-LAD
Clavines	9-Deacetoxyfumigaclavine C Agroclavine Chanoclavine Chanoclavine II Costaclavin Cycloclavine Elymoclavine Epoxyagroclavine Festuclavine Fumigaclavine A Fumigaclavine B Fumigaclavine C Paliclavine Penniclavine Setoclavine
Other ergolines	Acetergamine CY-208,243 Ergoline Lergotrile Nicergoline Pergolide
Natural sources	Achnatherum robustum (Sleepy Grass) Claviceps spp. (Ergot) Morning glory: Argyreia nervosa (Hawaiian Baby Woodrose), Ipomoea spp.(Morning Glory, Tlitliltzin, Badoh Negro), Rivea corymbosa (Coaxihuitl, Ololiúqui)