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AL-LAD
	;
Legal status
Legal status	; ; ; UK: Class A ; ; Illegal in Denmark, 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 N; ;
; PubChem CID;	; 15227511; ;
ChemSpider	; ; 21106248 Y; ;
UNII	; 020O2SR91L; ;
ChEMBL	; ; CHEMBL281787 Y; ;
Chemical and physical data
Formula	; C22H27N3O;
Molar mass	; 349.4713 g/mol
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 Y; ; Key:JCQLEPDZFXGHHQ-OXQOHEQNSA-N Y; ; ;
; NY (what is this?) (verify);

AL-LAD, also known as 6-allyl-6-nor-LSD, is a psychedelic drug and an analog of lysergic acid diethylamide (LSD).^[1] 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;^[2]^[3] an active dose of AL-LAD is reported to be between 50 and 150 micrograms.^[4] 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,^[5] 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.^[6]

Denmark

AL-LAD is illegal in Denmark.^[7]

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.^[8]

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.^[9]

Switzerland

AL-LAD is illegal in Switzerland.^[10]

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.^[11] 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,^[12] 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.^[13]

References

^ Simon D. Brandt; Pierce V. Kavanagh; Folker Westphal; Simon P. Elliott; Jason Wallach; Tristan Colestock; Timothy E. Burrow; Stephen J. Chapman; Alexander Stratford; David E. Nichols; Adam L. Halberstadt (June 2016). "Return of the lysergamides. Part II: Analytical and behavioural characterization of N6-allyl-6-norlysergic acid diethylamide (AL-LAD) and (2'S,4'S)-lysergic acid 2,4-dimethylazetidide (LSZ)". Drug Testing and Analysis. doi:10.1002/dta.1985. PMID 27265891..mw-parser-output cite.citationfont-style:inherit.mw-parser-output qquotes:"""""""'""'".mw-parser-output code.cs1-codecolor:inherit;background:inherit;border:inherit;padding:inherit.mw-parser-output .cs1-lock-free abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Lock-green.svg/9px-Lock-green.svg.png")no-repeat;background-position:right .1em center.mw-parser-output .cs1-lock-limited a,.mw-parser-output .cs1-lock-registration abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Lock-gray-alt-2.svg/9px-Lock-gray-alt-2.svg.png")no-repeat;background-position:right .1em center.mw-parser-output .cs1-lock-subscription abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Lock-red-alt-2.svg/9px-Lock-red-alt-2.svg.png")no-repeat;background-position:right .1em center.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registrationcolor:#555.mw-parser-output .cs1-subscription span,.mw-parser-output .cs1-registration spanborder-bottom:1px dotted;cursor:help.mw-parser-output .cs1-hidden-errordisplay:none;font-size:100%.mw-parser-output .cs1-visible-errorfont-size:100%.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration,.mw-parser-output .cs1-formatfont-size:95%.mw-parser-output .cs1-kern-left,.mw-parser-output .cs1-kern-wl-leftpadding-left:0.2em.mw-parser-output .cs1-kern-right,.mw-parser-output .cs1-kern-wl-rightpadding-right:0.2em

^ Fabrizio Schifano; Laura Orsolini; Duccio Papanti; John Corkery (June 2016). "NPS: Medical Consequences Associated with Their Intake". Current Topics in Behavioral Neurosciences. Springer International Publishing. pp. 1–30. doi:10.1007/7854_2016_15. ISSN 1866-3370. OCLC 643052237. PMID 27272067.

^ Hoffman AJ, Nichols DE; Nichols (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 0-9630096-9-9. 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.

^ "Archived copy" (PDF). Archived (PDF) from the original on 2017-10-31. Retrieved 2017-04-21.CS1 maint: Archived copy as title (link)

^ "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.

Additional literature

Watts, V. J.; Mailman, R. B.; Lawler, C. P.; Neve, K. A.; Nichols, D. E. (1995). "LSD and structural analogs: Pharmacological evaluation at D1 dopamine receptors". Psychopharmacology. 118 (4): 401–9. doi:10.1007/BF02245940. PMID 7568626.

Niwaguchi, T; Nakahara, Y; Ishii, H (1976). "Studies on lysergic acid diethylamide and related compounds. IV. Syntheses of various amide derivatives of norlysergic acid and related compounds". Yakugaku Zasshi. 96 (5): 673–8. PMID 987200.

Robert C. Pfaff, Xuemei Huang, Danuta Marona-Lewicka, Robert Oberlender and David E. Nichols: Lysergamides Revisited. In: NIDA Research Monograph 146: Hallucinogens: An Update. p. 52, 1994, United States Department of Health and Human Services.

External links

AL-LAD entry in TiHKAL

AL-LAD entry in TiHKAL • info

AL-LAD Thread at UKChemicalResearch.org

[1] Simon D. Brandt; Pierce V. Kavanagh; Folker Westphal; Simon P. Elliott; Jason Wallach; Tristan Colestock; Timothy E. Burrow; Stephen J. Chapman; Alexander Stratford; David E. Nichols; Adam L. Halberstadt (June 2016). "Return of the lysergamides. Part II: Analytical and behavioural characterization of N6-allyl-6-norlysergic acid diethylamide (AL-LAD) and (2'S,4'S)-lysergic acid 2,4-dimethylazetidide (LSZ)". Drug Testing and Analysis. doi:10.1002/dta.1985. PMID 27265891..mw-parser-output cite.citationfont-style:inherit.mw-parser-output qquotes:"""""""'""'".mw-parser-output code.cs1-codecolor:inherit;background:inherit;border:inherit;padding:inherit.mw-parser-output .cs1-lock-free abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Lock-green.svg/9px-Lock-green.svg.png")no-repeat;background-position:right .1em center.mw-parser-output .cs1-lock-limited a,.mw-parser-output .cs1-lock-registration abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Lock-gray-alt-2.svg/9px-Lock-gray-alt-2.svg.png")no-repeat;background-position:right .1em center.mw-parser-output .cs1-lock-subscription abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Lock-red-alt-2.svg/9px-Lock-red-alt-2.svg.png")no-repeat;background-position:right .1em center.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registrationcolor:#555.mw-parser-output .cs1-subscription span,.mw-parser-output .cs1-registration spanborder-bottom:1px dotted;cursor:help.mw-parser-output .cs1-hidden-errordisplay:none;font-size:100%.mw-parser-output .cs1-visible-errorfont-size:100%.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration,.mw-parser-output .cs1-formatfont-size:95%.mw-parser-output .cs1-kern-left,.mw-parser-output .cs1-kern-wl-leftpadding-left:0.2em.mw-parser-output .cs1-kern-right,.mw-parser-output .cs1-kern-wl-rightpadding-right:0.2em

[2] Fabrizio Schifano; Laura Orsolini; Duccio Papanti; John Corkery (June 2016). "NPS: Medical Consequences Associated with Their Intake". Current Topics in Behavioral Neurosciences. Springer International Publishing. pp. 1–30. doi:10.1007/7854_2016_15. ISSN 1866-3370. OCLC 643052237. PMID 27272067.

[pmid4032428-3] Hoffman AJ, Nichols DE; Nichols (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_26-4] Shulgin, Alexander (1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. p. 392. ISBN 0-9630096-9-9. Archived from the original on 2015-11-18.

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

[UNCPS-6] simone.rupprich. "Conventions". www.unodc.org. Archived from the original on 12 January 2018. Retrieved 4 May 2018.

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

[likumi.lv-8] "Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem". LIKUMI.LV. Archived from the original on 4 May 2018. Retrieved 4 May 2018.

[9] "Archived copy" (PDF). Archived (PDF) from the original on 2017-10-31. Retrieved 2017-04-21.CS1 maint: Archived copy as title (link)

[10] "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-11] 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-12] "PART 1308 - Section 1308.11 Schedule I". www.deadiversion.usdoj.gov. Archived from the original on 27 August 2009. Retrieved 4 May 2018.

[13] "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.

v t e Ergolines
Lysergic acid derivatives	2-Bromo-LSD (BOL-148) Bromocriptine Cabergoline Dihydroergocornine Dihydroergocristine Dihydroergocryptine Dihydroergometrine (Dihydroergonovine, Dihydroergobasine) Dihydroergosine Dihydroergotamine Epicriptine Ergine (LSA; LA-111; Lysergamide) Ergocornine Ergocristine Ergocryptine Ergoloid (Dihydroergotoxine) Ergometrine (Ergonovine, Ergobasine) Ergometrinine Ergotamine Ergotoxine Ergovaline Lisuride LSD LSH Lysergic Acid Lysergic acid cyclobutylamide Lysergic acid cyclopentylamide Lysergic Acid Methyl Ester Lysergol Mesulergine Metergoline Methergine (Methylergometrine, Methylergonovine, Methylergobasine) Methysergide Pergolide Syntometrine
Psychedelic lysergamides	1P-ETH-LAD 1P-LSD AL-LAD ALD-52 BU-LAD CYP-LAD DAL DAM-57 Ergonovine 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 Methylergonovine Methylisopropyllysergamide MLD-41 PARGY-LAD PRO-LAD
clavines	agroclavine elymoclavine lysergol festuclavine fumigaclavine A fumigaclavine B fumigaclavine C
Other ergolines	Ergoline
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)

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