LYSERGIDE TARTRATE

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C20H25N3O.C4H6O6
Molecular Weight	473.5188
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O[C@H]([C@@H](O)C(O)=O)C(O)=O.[H][C@@]12CC3=CNC4=C3C(=CC=C4)C1=C[C@H](CN2C)C(=O)N(CC)CC

InChI

InChIKey=HQMPRARIZOUKRO-AJLBZGGQSA-N

InChI=1S/C20H25N3O.C4H6O6/c1-4-23(5-2)20(24)14-9-16-15-7-6-8-17-19(15)13(11-21-17)10-18(16)22(3)12-14;5-1(3(7)8)2(6)4(9)10/h6-9,11,14,18,21H,4-5,10,12H2,1-3H3;1-2,5-6H,(H,7,8)(H,9,10)/t14-,18-;1-,2-/m11/s1

HIDE SMILES / InChI

Molecular Formula	C20H25N3O
Molecular Weight	323.432
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	C4H6O6
Molecular Weight	150.0868
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.emcdda.europa.eu/publications/drug-profiles/lsd | https://www.ncbi.nlm.nih.gov/pubmed/29147729 | https://www.ncbi.nlm.nih.gov/pubmed/27886063 | https://www.maps.org/research-archive/lsd/swisslsd/IB_LSD.pdf

Lysergide (LSD) is a semi-synthetic hallucinogen and is one of the most potent drugs known. Recreational use became popular between the 1960s to 1980s, but is now less common. LSD was first synthesized by Albert Hoffman while working for Sandoz Laboratories in Basel in 1938. Some years later, during a re-evaluation of the compound, he accidentally ingested a small amount and described the first ‘trip’. During the 1950s and 1960s, Sandoz evaluated the drug for therapeutic purposes and marketed it under the name Delysid®. It was used for research into the chemical origins of mental illness. Recreational use started in the 1960s and is associated with the ‘psychedelic period’. LSD possesses a complex pharmacological profile that includes direct activation of serotonin, dopamine and norepinephrine receptors. In addition, one of its chief sites of action is that of compound-specific (“allosteric”) alterations in secondary messengers associated with 5HT2A and 5HT2C receptor activation and changes in gene expression. The hallucinogenic effects of LSD are likely due to agonism at 5HT2A and 5HT2C receptors. LSD is also an agonist at the majority of known serotonin receptors, including 5HT1A, 5HT1B, 5HT1D, 5HT5A, 5HT6 and 5HT7 receptors. During the 1960s, LSD was investigated for a variety of psychiatric indications, including the following: as an aid in treatment of schizophrenia; as a means of creating a "model psychosis"; as a direct antidepressant; and as an adjunct to psychotherapy. LSD is listed in Schedule I of the United Nations 1971 Convention on Psychotropic Substances.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Serotonin 1a (5-HT1a) receptor 171 Target ID: CHEMBL214 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28447622 \| https://www.ncbi.nlm.nih.gov/pubmed/12213075	Agonist 2662	0.003 µM [Ki]
Serotonin 2a (5-HT2a) receptor 230 Target ID: CHEMBL224 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8663249 \| https://www.ncbi.nlm.nih.gov/pubmed/28447622	Agonist 2662	0.004 µM [Ki]
Serotonin 2c (5-HT2c) receptor 122 Target ID: CHEMBL225 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10611640 \| https://www.ncbi.nlm.nih.gov/pubmed/28447622	Agonist 2662	0.015 µM [Ki]
Serotonin 6 (5-HT6) receptor 45 Target ID: CHEMBL3371 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9730917 \| https://www.ncbi.nlm.nih.gov/pubmed/14613313	Agonist 2662	6.31 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Anxiety 266 Sources: https://clinicaltrials.gov/ct2/show/NCT00920387	Primary		Phase II 1144	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
3.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28197931/	200 μg single, oral dose: 200 μg route of administration: Oral experiment type: SINGLE co-administered:		LYSERGIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1.3 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28197931/	100 μg single, oral dose: 100 μg route of administration: Oral experiment type: SINGLE co-administered:		LYSERGIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
20.3 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28197931/	200 μg single, oral dose: 200 μg route of administration: Oral experiment type: SINGLE co-administered:		LYSERGIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
8.1 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28197931/	100 μg single, oral dose: 100 μg route of administration: Oral experiment type: SINGLE co-administered:		LYSERGIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28197931/	200 μg single, oral dose: 200 μg route of administration: Oral experiment type: SINGLE co-administered:		LYSERGIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
2.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28197931/	100 μg single, oral dose: 100 μg route of administration: Oral experiment type: SINGLE co-administered:		LYSERGIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1579 substrate 1709	substrate 1010 inhibitor 1752	inhibitor 1837 substrate 1193

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1437 CYP19A1 58	FMO3 66 CYP2C8 688 CYP2A6 523 CYP2E1 648 CYP2C19 985 CYP1A2 1032 CYP2B6 660 CYP3A5 391

Drug as perpetrator

Target	Modality	Activity
CYP2D6 1875	inhibitor 3240 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645840#sid=144206425	inconclusive [IC50 0.9296 uM]
P-gp 1626	inhibitor 3240 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1346987#sid=144207057	inconclusive [IC50 23.1093 uM]
CYP2C9 1803	inhibitor 3240 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645842#sid=144206425	inconclusive [IC50 82.8488 uM]
CYP3A4 1909	inhibitor 3240 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645841#sid=144206425	inconclusive [IC50 82.8488 uM]
CYP19A1 58	inhibitor 3240 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/743139#sid=144206425	no

Drug as victim

Target	Modality	Activity
CYP2A6 523	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/30617391/	no
CYP2B6 660	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/30981875/	no
CYP2C19 985	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/30981875/	no
CYP2C8 688	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/30981875/	no
CYP3A5 391	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/30617391/	no
FMO3 66	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/30617391/	no
CYP1A2 1032	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/30981875/	yes
CYP2C9 1010	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/30981875/	yes
CYP2D6 1193	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/30981875/	yes
CYP2E1 648	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/30981875/	yes
CYP3A4 1709	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/30981875/	yes

Sourcing

Vendor/Aggregator	ID	URL
Compound Cloud	5761
HongKong Chemhere	SCA48653
MuseChem	R060199	https://www.musechem.com/product/R060199.html
Tetrahedron	TS77453	http://www.thsci.com/search.do?q=TS77453
Toronto Research Chemicals	KIT0380	https://www.trc-canada.com/product-detail/?CatNum=KIT0380
Toronto Research Chemicals	KIT1587	https://www.trc-canada.com/product-detail/?CatNum=KIT1587
Toronto Research Chemicals	L488010	https://www.trc-canada.com/product-detail/?CatNum=L488010
eMolecules	105346456	https://orderbb.emolecules.com/search/#?query=105346456
eMolecules	260954711	https://orderbb.emolecules.com/search/#?query=260954711
eMolecules	261082209	https://orderbb.emolecules.com/search/#?query=261082209

PubMed

Title	Date	PubMed
[Chemical structure and lysergic acid derivative psychoses].	1956 Aug 9	13359249
Psychopathology and psychophysiology of minimal LSD-25 dosage; a preliminary dosage-response spectrum.	1958 Feb	13497365
PERSISTENCE OF LYSERGIC ACID DIETHYLAMIDE IN THE PLASMA OF HUMAN SUBJECTS.	1964 Sep-Oct	14209776
Hallucinogens and Drosophila: linking serotonin receptor activation to behavior.	2002	12435434
Flashback and Hallucinogen Persisting Perception Disorder: clinical aspects and pharmacological treatment approach.	2002	12227234
Lysergic acid diethylamide-induced Fos expression in rat brain: role of serotonin-2A receptors.	2002	12220572
[Current drugs. New clinical problems].	2002	12145841
LSD therapy in Dutch psychiatry: changing socio-political settings and medical sets.	2002 Apr	12024809
Immunoassay screening of lysergic acid diethylamide (LSD) and its confirmation by HPLC and fluorescence detection following LSD ImmunElute extraction.	2002 Apr	11991536
Drugs of abuse monitoring in blood for control of driving under the influence of drugs.	2002 Apr	11897967
Exposure opportunity as a mechanism linking youth marijuana use to hallucinogen use.	2002 Apr 1	11906800
Chemical casualties. Centrally acting incapacitants.	2002 Dec	12703427
The hallucinogen d-lysergic acid diethylamide (d-LSD) induces the immediate-early gene c-Fos in rat forebrain.	2002 Dec 27	12470860
An analysis of the utility of differential outcome procedures in drug discrimination research.	2002 Jul	12218507
Optimization of the separation of lysergic acid diethylamide in urine by a sweeping technique using micellar electrokinetic chromatography.	2002 Jul 25	12101058
NHS settles claim of patients treated with LSD.	2002 Mar 2	11872538
A single dose of lysergic acid diethylamide influences gene expression patterns within the mammalian brain.	2002 May	11927188
Comparison of EMIT II, CEDIA, and DPC RIA assays for the detection of lysergic acid diethylamide in forensic urine samples.	2002 Oct	12423010
The effects of psychotomimetics and psychomotor stimulants on two schedules promoting response switching in the rat.	2002 Oct	12373438
[Hawaiian baby woodrose: (Psycho-) Pharmacological effects of the seeds of Argyreia nervosa. A case-orientated demonstration].	2002 Sep	12215884
Differential activation of Gq/11 and Gi(3) proteins at 5-hydroxytryptamine(2C) receptors revealed by antibody capture assays: influence of receptor reserve and relationship to agonist-directed trafficking.	2002 Sep	12181434
Lysergamides of isomeric 2,4-dimethylazetidines map the binding orientation of the diethylamide moiety in the potent hallucinogenic agent N,N-diethyllysergamide (LSD).	2002 Sep 12	12213075
A common oscillator for perceptual rivalries?	2003	12729381
Prevalence and risk factors for LSD use among young women.	2003 Apr	12742139
Discovering risperidone: the LSD model of psychopathology.	2003 Apr	12669030
[Clinical methods in evolutional physiology].	2003 Jan-Feb	12739261
Synthesis and pharmacological characterization of a series of geometrically constrained 5-HT(2A/2C) receptor ligands.	2003 Jul 31	12877591
Case report: an ingestion of Hawaiian Baby Woodrose seeds associated with acute psychosis.	2003 Jun	12886727
The effective treatment of acne vulgaris by a high-intensity, narrow band 405-420 nm light source.	2003 Jun	12850803
Effects of autoshaping procedures on 3H-8-OH-DPAT-labeled 5-HT1a binding and 125I-LSD-labeled 5-HT2a binding in rat brain.	2003 Jun 13	12763605
Blue light (clearlight) for acne vulgaris.	2003 Jun 23	12817196
Enhancing action of LSD on neuronal responsiveness to serotonin in a brain structure involved in obsessive-compulsive disorder.	2003 Mar	12899732
Persisting visual hallucinations and illusions in previously drug-addicted patients.	2003 Mar	12664374
Determination of lysergic acid diethylamide (LSD) in mouse blood by capillary electrophoresis/ fluorescence spectroscopy with sweeping techniques in micellar electrokinetic chromatography.	2003 Mar	12658692
On-line identification of lysergic acid diethylamide (LSD) in tablets using a combination of a sweeping technique and micellar electrokinetic chromatography/77 K fluorescence spectroscopy.	2003 Mar	12658691
Salvinorin A: the "magic mint" hallucinogen finds a molecular target in the kappa opioid receptor.	2003 Mar	12628350
Clonazepam treatment of lysergic acid diethylamide-induced hallucinogen persisting perception disorder with anxiety features.	2003 Mar	12598822
Creation, expression, and characterization of a constitutively active mutant of the human serotonin 5-HT6 receptor.	2003 Mar	12494404
Hallucinogen persisting perception disorder: what do we know after 50 years?	2003 Mar 1	12609692
Dynamic changes in prefrontal cortex gene expression following lysergic acid diethylamide administration.	2003 Mar 17	12654518
Acute effects of drugs of abuse.	2003 Mar-Apr	12737367
Effect of the 5-HT6 receptor antagonists Ro04-6790 and Ro65-7199 on latent inhibition and prepulse inhibition in the rat: comparison to clozapine.	2003 May	12873617
The development and application of a gas chromatography-mass spectrometric (GC-MS) assay to determine the presence of 2-oxo-3-hydroxy-LSD in urine.	2003 May-Jun	12820748
Pharmacological characterization of a serotonin receptor (5-HT7) stimulating cAMP production in human corneal epithelial cells.	2003 Nov	14578406
Serotonin receptors in platelets of bipolar and schizoaffective patients: effect of lithium treatment.	2003 Nov	12845409
LC-MS analysis of 2-oxo-3-hydroxy LSD from urine using a Speedisk positive-pressure processor with Cerex PolyChrom CLIN II columns.	2003 Oct	14607000
Transcriptome fingerprints distinguish hallucinogenic and nonhallucinogenic 5-hydroxytryptamine 2A receptor agonist effects in mouse somatosensory cortex.	2003 Oct 1	14523084
Biochemical outcome of blocking the ergot alkaloid pathway of a grass endophyte.	2003 Oct 22	14558758
Role of the serotonin 5-HT(2A) receptor in learning.	2003 Sep-Oct	14557608
Serotonergic/glutamatergic interactions: the effects of mGlu2/3 receptor ligands in rats trained with LSD and PCP as discriminative stimuli.	2004 Mar	14598016

Patents

Sample Use Guides

In Vivo Use Guide

Lysergide (LSD) is active at doses from about 20 ug. Typical doses are now about 20 to 80 ug although, in the past, doses as high as 300 ug were common.

Route of Administration: Oral

In Vitro Use Guide

Lysergide (LSD) (3-100 nM) and DOI (0.3-10 uM) excited almost every cell excited by 5-HT. The maximal excitation achieved with LSD and DOI was 39% and 55% of the effect of a near-maximal 5-HT concentration (100 uM).

Substance Class	Chemical Created by `admin` on `Wed Jul 05 22:41:29 UTC 2023` Edited by `admin` on `Wed Jul 05 22:41:29 UTC 2023`
Record UNII	KXF3755R6D
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LYSERGIDE TARTRATE

Common Name

English

LYSERGIC ACID DIETHYLAMIDE BITARTRATE

Common Name

English

Lysergic Acid Diethylamide Tartrate

Common Name

English

ERGOLINE-8-CARBOXAMIDE, 9,10-DIDEHYDRO-N,N-DIETHYL-6-METHYL-, (8.BETA.)-, (R-(R*,R*))-2,3-DIHYDROXYBUTANEDIOATE (1:1)

Systematic Name

English

ERGOLINE-8-CARBOXAMIDE, 9,10-DIDEHYDRO-N,N-DIETHYL-6-METHYL-, (8.BETA.)-, (2R,3R)-2,3-DIHYDROXYBUTANEDIOATE (1:1)

Systematic Name

English

LSD BITARTRATE

Common Name

English

Code System Code Type Description

FDA UNII

KXF3755R6D