From Surf Wiki (app.surf) — the open knowledge base
ETH-LAD
Chemical compound
Chemical compound
| Field | Value | |||
|---|---|---|---|---|
| Verifiedfields | verified | |||
| Watchedfields | verified | |||
| verifiedrevid | 414446334 | |||
| image | ETH-LAD v2.svg | |||
| image_class | skin-invert-image | |||
| width | 175px | |||
| image2 | ETH-LAD 3D.png | |||
| image_class2 | bg-transparent | |||
| width2 | 200px | |||
| routes_of_administration | Oral | |||
| class | Serotonin receptor agonist; Serotonergic psychedelic; Hallucinogen | |||
| legal_DE | NpSG | |||
| legal_UK | Class A | |||
| legal_status | Illegal in France | |||
| onset | 15 minutes–1 hour | |||
| duration_of_action | 8–12 hours | |||
| CAS_number_Ref | ||||
| CAS_number | 65527-62-0 | |||
| PubChem | 44457783 | |||
| ChemSpiderID_Ref | ||||
| ChemSpiderID | 21106300 | |||
| ChEMBL_Ref | ||||
| ChEMBL | 22694 | |||
| UNII_Ref | ||||
| UNII | 21Z2736X9Q | |||
| synonyms | ETH-LAD; ETHLAD; 6-Ethyl-6-nor-lysergic acid diethylamide; 6-Ethyl-6-nor-LSD; *N*(6)-Ethyl-nor-LSD; 9,10-Didehydro-*N*,*N*,6-triethylergoline-8β-carboxamide | |||
| IUPAC_name | (6a*R*,9*R*)-*N*,*N*-diethyl-7-ethyl-4,6,6a,7,8,9- | |||
| hexahydroindolo-[4,3-*fg*]quinoline-9-carboxamide | ||||
| C | 21 | H=27 | N=3 | O=1 |
| SMILES | CCN(C([C@@H]1C=C2C3=CC=CC4=C3C(C[C@H]2N(CC)C1)=CN4)=O)CC | |||
| StdInChI_Ref | ||||
| StdInChI | 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 | |||
| StdInChIKey_Ref | ||||
| StdInChIKey | MYNOUXJLOHVSMQ-DNVCBOLYSA-N |
| elimination_half-life =
hexahydroindolo-[4,3-fg]quinoline-9-carboxamide
ETH-LAD, or ETHLAD, also known as 6-ethyl-6-nor-LSD, is a psychedelic drug of the lysergamide family related to lysergic acid diethylamide (LSD; also known as METH-LAD). It is slightly more potent than LSD and is among the most potent psychedelics known. The drug is taken orally.
It acts as a serotonin receptor agonist, including of the serotonin 5-HT2A receptor. In addition, it binds to dopamine receptors. The drug produces psychedelic-like effects in animals. It is closely structurally related to LSD and to other psychedelic lysergamides like PRO-LAD and AL-LAD.
ETH-LAD was first described in the scientific literature by 1976. Its effects in humans were assessed and reported by Alexander Shulgin in the 1980s and 1990s. The drug was encountered as a novel recreational designer drug in Europe by 2016. In addition, a prodrug of ETH-LAD, 1P-ETH-LAD, has been developed and encountered as a designer drug.
Use and effects
According to Alexander Shulgin in his book TiHKAL (Tryptamines I Have Known and Loved), ETH-LAD has a dose of 40 to 150μg orally and a duration of 8 to 12hours. However, it also produced clear effects at a dose of 20μg, and in other publications, Shulgin gave a lower dose range for the drug of 40 to 80μg. Its onset ranges from 15minutes to 1hour and peak effects occur after about 1 to 2hours.
Shulgin has stated that ETH-LAD is "a little more potent" than LSD or roughly twice as potent as LSD in humans. Other researchers have described it as "slightly more potent" or "somewhat more potent" than LSD in humans. For comparison, Shulgin lists the dose range of LSD as 60 to 200μg or 50 to 200μg in his publications. Based on the preceding findings, ETH-LAD is one of the most potent serotonergic psychedelics known in humans, if not the most potent known psychedelic. As a result of this, it has been said that LSD can no longer be considered the most potent psychedelic.
The effects of ETH-LAD have been reported to include closed-eye imagery, very few visual changes or distortions, gentle movements of objects, LSD-like visual aspects, two-dimensional surfaces looking three-dimensional, objects looking "magical", and possible time slowing. It was described as making the body feel balanced, thinking being easy, concepts easy to follow through, mind capable of realistic and down-to-earth thought, and warmth and humor being present. Other reported effects included feeling lazy, diuretic effects, no appetite loss, decongestant effects, stomach discomfort, and chills.
Compared to LSD, ETH-LAD was described as lacking the push and sparkle of LSD, allowing for extraordinary experiences with none of LSD's demands, being less aggressive than LSD and lacking its "taking control" nature, having a greatly modified degree of visual distortion relative to LSD, having visual effects similar to LSD but much more gentle, and being more allowing than demanding.
Interactions
Pharmacology
Pharmacodynamics
ETH-LAD acts as a serotonin receptor agonist, including of the serotonin 5-HT2A receptor. It shows greater potency and efficacy as a serotonin 5-HT2A receptor agonist than LSD in vitro. In addition to the serotonin 5-HT2A receptor, the drug binds with high affinity to the serotonin 5-HT1A and 5-HT2C receptors. Like LSD, ETH-LAD also binds with lower affinity to the dopamine D1, D2, D3, D4, and D5 receptors.
ETH-LAD shows psychedelic-like effects in animals, specifically rodent drug discrimination tests. It is about 1.6- to 2.3-fold more potent than LSD in these tests. Similarly to LSD, ETH-LAD shows moderate anti-inflammatory effects in preclinical research, but with slightly higher potency.
Pharmacokinetics
The in-vitro metabolism of ETH-LAD has been studied.
Chemistry
ETH-LAD, also known as 9,10-didehydro-N,N,6-triethylergoline-8β-carboxamide or as 6-ethyl-6-nor-LSD, is a substituted lysergamide derivative related to lysergic acid diethylamide (LSD; also known as METH-LAD). It is the 6-ethyl derivative of nor-LSD (6-nor-LSD; H-LAD) and is the derivative of LSD with an ethyl group instead of methyl group at the 6 position of the ergoline ring system.
Properties
According to Alexander Shulgin, ETH-LAD may be chemically unstable in solution.
Synthesis
The chemical synthesis of ETH-LAD has been described.
Analogues
Analogues of ETH-LAD include nor-LSD, LSD, PRO-LAD, IP-LAD, AL-LAD, FLUORETH-LAD, and CE-LAD, among others. 1P-ETH-LAD, a prodrug of ETH-LAD, has been developed and encountered as a novel designer drug.
History
ETH-LAD was first described in the scientific literature by Tetsukichi Niwaguchi and colleagues by 1976. Subsequently, its preclinical pharmacology was studied and described by Andrew J. Hoffman and David E. Nichols in 1985. ETH-LAD's properties and effects in humans were assessed by Alexander Shulgin. These observations were reported via personal communication by Nichols in 1986, later described by Shulgin himself in a 1994 literature review, and described in-depth by Shulgin himself in his 1997 book TiHKAL (Tryptamines I Have Known and Loved). ETH-LAD was encountered as a novel designer drug in Europe by 2016.
Society and culture
Legal status
Canada
ETH-LAD is not a controlled substance in Canada as of 2025.
Switzerland
ETH-LAD is illegal in Switzerland as of December 2015.
United Kingdom
On June 10, 2014, the United Kingdom Advisory Council on the Misuse of Drugs (ACMD) recommended that ETH-LAD be specifically named in the UK Misuse of Drugs Act as a class A drug despite not identifying it as ever having been sold or any harm associated with its use. The UK Home office accepted this advice and announced a ban of the substance to be enacted on 6 January 2015.
United States
ETH-LAD is not an explicitly controlled substance in the United States. However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.
References
References
- (20 May 2021). "Arrêté du 20 mai 2021 modifiant l'arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants".
- (2013). "Biological Research on Addiction: Comprehensive Addictive Behaviors and Disorders". Elsevier.
- (1991). "Biochemistry and Physiology of Substance Abuse". CRC Press.
- (1994). "Lysergamides revisited". NIDA Research Monograph.
- (2018). "Chemistry and Structure-Activity Relationships of Psychedelics".
- (1994). "Structure-activity relationships of the classic hallucinogens and their analogs". NIDA Res Monogr.
- (February 1986). "Studies of the Relationship Between Molecular Structure and Hallucinogenic Activity". Pharmacol Biochem Behav.
- (23 October 2018). "EMCDDA–Europol 2016 Annual Report on the implementation of Council Decision 2005/387/JHA".
- (October 2024). "Chemistry/structural biology of psychedelic drugs and their receptor(s)". Br J Pharmacol.
- (October 2017). "Return of the lysergamides. Part III: Analytical characterization of N6 -ethyl-6-norlysergic acid diethylamide (ETH-LAD) and 1-propionyl ETH-LAD (1P-ETH-LAD)". Drug Test Anal.
- (2003). "Hallucinogens: A Forensic Drug Handbook". Elsevier Science.
- (May 1989). "Stereoselective aspects of hallucinogenic drug action and drug discrimination studies of entactogens". Purdue University.
- (16 January 2013). "Mapping the binding site of the 5-HT2A receptor using mutagenesis and ligand libraries: Insights into the molecular actions of psychedelics". Purdue University.
- (April 2021). "Structure-Activity Relationship Analysis of Psychedelics in a Rat Model of Asthma Reveals the Anti-Inflammatory Pharmacophore". ACS Pharmacol Transl Sci.
- (April 1995). "LSD and structural analogs: pharmacological evaluation at D1 dopamine receptors". Psychopharmacology.
- (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.
- (July 2019). "In vitro metabolic fate of nine LSD-based new psychoactive substances and their analytical detectability in different urinary screening procedures". Anal Bioanal Chem.
- (2024). "The use of prodrugs as drugs of abuse". WIREs Forensic Science.
- (1976). "Lysergic Acid Diethylamideおよび関連化合物に関する研究(第4報)Norlysergic Acidの各種Amide誘導体ならびに関連化合物の合成". Yakugaku Zasshi.
- {{CiteTiHKAL
- "Controlled Drugs and Substances Act".
- "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien". Der Bundesrat.
- Advisory Council on the Misuse of Drugs (ACMD). (10 June 2014). "Update of the Generic Definition for Tryptamines". UK Home Office.
- "The Misuse of Drugs Act 1971 (Amendment) (No. 2) Order 2014".
- (January 2026). "Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026)". U.S. [[Department of Justice]]: [[Drug Enforcement Administration]] (DEA): Diversion Control Division.
This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.
Ask Mako anything about ETH-LAD — get instant answers, deeper analysis, and related topics.
Research with MakoFree with your Surf account
Create a free account to save articles, ask Mako questions, and organize your research.
Sign up freeThis content may have been generated or modified by AI. CloudSurf Software LLC is not responsible for the accuracy, completeness, or reliability of AI-generated content. Always verify important information from primary sources.
Report