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Description

ETH-LAD Also known as:

  • (8β)-N,N,6-Triethyl-9,10-didehydroergolin-8-carboxamid[German][ACD/IUPAC Name]
  • (8β)-N,N,6-Triethyl-9,10-didehydroergoline-8-carboxamide[ACD/IUPAC Name]
  • (8β)-N,N,6-Triéthyl-9,10-didéhydroergoline-8-carboxamide[French][ACD/IUPAC Name]
  • Ergoline-8-carboxamide, 9,10-didehydro-N,N,6-triethyl-, (8β)-[ACD/Index Name]
  • N-ETHYLNORLYSERGIC ACID N,N-DIETHYLAMIDE
  • 6-ethyl-9,10-didehydro-ergoline-8-carboxylic acid diethylamide
  • 7-Ethyl-4,6,6a,7,8,9-hexahydro-indolo[4,3-fg]quinoline-9-carboxylic acid diethylamide
  • Ergoline-8-carboxamide, 9,10-didehydro-N,N,6-triethyl-, (8b)-
  • ETH-LAD
  • N,N,6-triethyl-9,10-didehydroergolin-8-carboxamide[ACD/IUPAC Name]
  • N-Ethyl Norlysergic Acid N,N-Diethylamide

A psychedelic drug and slightly more potent analogue of LSD, first synthesised by Alexander Shulgin - sometimes described as being less ‘abrasive’ than LSD. Less common than the associated AL-LAD, though has seen some popularity since its release on the Internet research chemical scene in 2015.

Summary

ETH-LAD is chemically similar to LSD and has a similar mechanism of action, acting primarily by stimulating serotonin receptors in the brain. The human use of ETH-LAD was first documented by Alexander Shulgin in his 1997 book TiHKAL ("Tryptamines I Have Known and Loved"). It is noted for its "modified visual distortion" relative to LSD.

It has been marketed alongside psychedelic lysergamides like 1P-LSD and AL-LAD as a legal, grey-market alternative to LSD, and commercially distributed through online research chemical vendors. ETH-LAD has been shown to be moderately to significantly more potent than LSD itself in animal studies with an active dose reported at between 40 and 100 micrograms. Anecdotal reports suggest that while it produces similar effects to LSD at low to common doses, it displays a notably divergent effects profile at higher doses, sometimes described as producing “algorithmic” and “warped” visual and auditory distortions, combined with a more “introspective” and “analytical”, if not more “neutral” head space.

ETH-LAD has also been reported to more readily produce adverse physical effects such as severe and persisting nausea, temperature dysregulation, and generalized bodily discomfort, particularly at higher doses. This has been speculated to owe itself to an unusually sensitive and unpredictable dose-response curve, as low to common dose experiences are generally described as being very manageable and non-threatening. Very little data exists about the pharmacological properties, metabolism, and toxicity of ETH-LAD, and it has little history of human usage.

Along with its sensitive dose-response and potentially concerning physical side effects, many reports suggest that this substance may be overly difficult to use safely for those who are not experienced with hallucinogens. It is highly advised to use harm reduction practices if using this substance.

Chemistry

ETH-LAD is a structural analog of lysergic acid with an N,N-diethylamide functional group bound to RN of the chemical structure.

This core polycyclic structure is an indole derivative and has both overlapping tryptamine and phenethylamine skeletons embedded within its molecular structure (although it is principally classified as a tryptamine).

ETH-LAD’s structure contains a bicyclic hexahydroindole fused to a bicyclic quinoline group (nor-lysergic acid). ETH-LAD does not contain a methyl group substituted at R6 of its nor-lysergic acid skeleton as is the case with LSD; this is represented by the nor- prefix.

Instead, ETH-LAD is substituted at R6 with an ethyl group.

At carbon 8 of the quinoline, a N,N-diethyl carboxamide is bound in the same configuration of LSD. ETH-LAD is a chiral compound with two stereocenters at R5 and R8.

ETH-LAD, also called (+)-D-ETH-LAD, has an absolute configuration of (5R, 8R).

Common NameN-ETHYLNORLYSERGIC ACID N,N-DIETHYLAMIDE
Systematic nameN-ETHYLNORLYSERGIC ACID N,N-DIETHYLAMIDE
FormulaC_{21}H_{27}N_{3}O
SMILESCCN1C[C@@H](C=C2[C@H]1Cc3c[nH]c4c3c2ccc4)C(=O)N(CC)CC
Std. InChiInChI=1S/C21H27N3O/c1-4-23(5-2)21(25)15-10-17-16-8-7-9-18-20(16)14(12-22-18)11-19(17)24(6-3)13-15/h7-10,12,15,19,22H,4-6,11,13H2,1-3H3/t15-,19-/m1/s1
Std. InChiKeyMYNOUXJLOHVSMQ-DNVCBOLYSA-N
Avg. Mass337.4586 Da
Molecular Weight337.4586
Monoisotopic Mass337.215424 Da
Nominal Mass337
ChemSpider ID21106300

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Dose Chart

Oral
Threshold20-30ug
Light30-60ug
Common60-100ug
Strong100-200ug+

Duration Chart

ETH-LAD Duration Data
Onset15-90 minutes
Duration6-14 hours
After-effects1-12 hours

Legal Status

ETH-LAD is currently a gray area compound within many parts of the world. This means that it is not known to be specifically illegal within most countries. People may still be charged for its possession under certain circumstances such as under analogue laws (as an analogue of LSD) and with the intent to sell or consume.

  • Austria: ETH-LAD is technically not illegal but it may fall in the NPSG (Neue-Psychoaktive-Substanzen-Gesetz Österreich) as an analogue of LSD.

  • Germany: ETH-LAD is controlled under the NpSG (New Psychoactive Substances Act) as of July 18, 2019. Production and import with the aim to place it on the market, administration to another person and trading is punishable. Possession is illegal but not penalized.
  • Latvia: ETH-LAD is illegal in Latvia. Although ETH-LAD is not officially scheduled, it is controlled as an LSD structural analog due to an amendment made on June 1, 2015.
  • Poland: ETH-LAD is a NPS class drug in Poland, making it illegal to possess or distribute.
  • Switzerland: ETH-LAD is scheduled as of the of December 1, 2015.
  • United Kingdom: As of January 7, 2015, ETH-LAD is specifically named in the U.K. Misuse of Drugs Act as a Class A controlled substance.
  • United States: ETH-LAD is unscheduled in the United States. It may be considered an analogue of LSD (which is a Schedule I compound under the Controlled Substances Act). As such, the sale for human consumption or the use for illicit non-medical or scientific research could be prosecuted as crimes under the Federal Analogue Act.

    • Sources

    References

    1. "COMPOUND SUMMARY: N-Ethylnorlysergic acid N,N-diethylamide". National Center for Biotechnology Information. CID 44457783. Retrieved May 5, 2017.
    2. Shulgin, Alexander; Shulgin, Ann (1997). "#12. ETH-LAD". TiHKAL: The Continuation. United States: Transform Press.  0-9630096-9-9. OCLC 38503252.
    3. Hoffman, Andrew J.; Nichols, David E. (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): 1252–1255. :10.1021/jm00147a022.  0022-2623.
    4. 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. :10.1007/BF03161089.  1556-9039.
    5. "Anlage NpSG" (in German). Bundesministerium der Justiz und für Verbraucherschutz [Federal Ministry of Justice and Consumer Protection]. Retrieved December 10, 2019.
    6. "Verordnung zur Änderung der Anlage des Neue-psychoaktive-Stoffe-Gesetzes und von Anlagen des Betäubungsmittelgesetzes" (PDF). Bundesgesetzblatt Jahrgang 2019 Teil I Nr. 27 (in German). Bundesanzeiger Verlag. July 17, 2019. pp. 1083–1094. Retrieved January 1, 2020.
    7. "§ 4 NpSG" (in German). Bundesministerium der Justiz und für Verbraucherschutz [Federal Ministry of Justice and Consumer Protection]. Retrieved December 10, 2019.
    8. "Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem" (in Latvian). VSIA Latvijas Vēstnesis. November 10, 2005. Retrieved January 1, 2020.
    9. "Rozporządzenie Ministra zdrowia z dnia 21 sierpnia 2019 r. zmieniające rozporządzenie w sprawie wykazu substancji psychotropowych, środków odurzających oraz nowych substancji psychoaktywnych" (PDF) (in Polish).
    10. "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel,psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien: Änderung vom 2. November 2015" (PDF) (in German). Bundeskanzlei [Federal Chancellery of Switzerland]. Retrieved January 1, 2020.
    11. Advisory Council on the Misuse of Drugs (June 10, 2014). "Update of the generic definition for tryptamines" (PDF). Government Digital Service. p. 12. Retrieved January 1, 2020.

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    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

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