LYSERGIDE TARTRATE

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	C4H6O6
Molecular Weight	150.0868
Charge	0
Count

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

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

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 172 Target ID: CHEMBL214 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28447622 \| https://www.ncbi.nlm.nih.gov/pubmed/12213075	Agonist 2678	0.003 µM [Ki]
Serotonin 2a (5-HT2a) receptor 231 Target ID: CHEMBL224 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8663249 \| https://www.ncbi.nlm.nih.gov/pubmed/28447622	Agonist 2678	0.004 µM [Ki]
Serotonin 2c (5-HT2c) receptor 124 Target ID: CHEMBL225 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10611640 \| https://www.ncbi.nlm.nih.gov/pubmed/28447622	Agonist 2678	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 2678	6.31 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Anxiety 267 Sources: https://clinicaltrials.gov/ct2/show/NCT00920387	Primary		Phase II 1132	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 1587 substrate 1737	substrate 1037 inhibitor 1767	inhibitor 1852 substrate 1217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1461 CYP19A1 60	FMO3 67 CYP2C8 693 CYP2A6 543 CYP2E1 667 CYP2C19 991 CYP1A2 1054 CYP2B6 664 CYP3A5 395

Drug as perpetrator

Target	Modality	Activity
CYP2D6 1891	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645840#sid=144206425	inconclusive [IC50 0.9296 uM]
P-gp 1650	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1346987#sid=144207057	inconclusive [IC50 23.1093 uM]
CYP2C9 1819	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645842#sid=144206425	inconclusive [IC50 82.8488 uM]
CYP3A4 1925	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645841#sid=144206425	inconclusive [IC50 82.8488 uM]
CYP19A1 60	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/743139#sid=144206425	no

Drug as victim

Target	Modality	Activity
CYP2A6 543	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/30617391/	no
CYP2B6 664	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/30981875/	no
CYP2C19 991	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/30981875/	no
CYP2C8 693	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/30981875/	no
CYP3A5 395	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/30617391/	no
FMO3 67	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/30617391/	no
CYP1A2 1054	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/30981875/	yes
CYP2C9 1037	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/30981875/	yes
CYP2D6 1217	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/30981875/	yes
CYP2E1 667	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/30981875/	yes
CYP3A4 1737	substrate 3367 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
Acute injection of drugs with low addictive potential (delta(9)-tetrahydrocannabinol, 3,4-methylenedioxymethamphetamine, lysergic acid diamide) causes a much higher c-fos expression in limbic brain areas than highly addicting drugs (cocaine and morphine).	1999 Aug 25	10521585
Reconstitution of human 5-hydroxytryptamine5A receptor--G protein coupling in E. coli and Sf9 cell membranes with membranes from Sf9 cells expressing mammalian G proteins.	2001	11697235
[Pharmacokinetic and toxicokinetic parameters of some drugs of abuse].	2001	11450374
Human 5-HT(5) receptors: the 5-HT(5A) receptor is functional but the 5-HT(5B) receptor was lost during mammalian evolution.	2001 Apr 27	11343685
Amphetamine, 3,4-methylenedioxymethamphetamine, lysergic acid diethylamide, and metabolites of the catecholamine neurotransmitters are agonists of a rat trace amine receptor.	2001 Dec	11723224
Selective and divergent regulation of cortical 5-HT(2A) receptors in rabbit.	2001 Dec	11714896
Determination of LSD and its metabolites in human biological fluids by high-performance liquid chromatography with electrospray tandem mass spectrometry.	2001 Dec 5	11817305
Lysergic acid diethylamide.	2001 Jul-Aug	11693215
A case study of space-time distortion during a total lunar eclipse following street use of LSD.	2001 Jul-Sep	11718324
Improvement of hallucinogen persisting perception disorder by treatment with a combination of fluoxetine and olanzapine: case report.	2001 Jun	11386500
Association of a 5-HT(5A) receptor polymorphism, Pro15Ser, to schizophrenia.	2001 Mar	11317225
Serotonergic function in major depression and effect of sertraline and paroxetine treatment.	2001 Mar	11236074
[Interferon alpha-associated agranulocytosis during clozapine treatment. Case report and status of current knowledge].	2001 Nov	11758095
Is the U.S. experiencing an incipient epidemic of hallucinogen use?	2001 Oct	11758819
EEG coherence in post-LSD visual hallucinations.	2001 Oct 1	11566431
Hallucinogens and Drosophila: linking serotonin receptor activation to behavior.	2002	12435434
Identification of a dopamine receptor from Caenorhabditis elegans.	2002 Feb 8	11814642
False-positive lysergic acid diethylamide immunoassay screen associated with fentanyl medication.	2002 Jan	11751564
Jekyll and Hyde revisited: paradoxes in the appreciation of drug experiences and their effects on creativity.	2002 Jul-Sep	12422935
Hallucinogens and redemption.	2002 Jul-Sep	12422934
Poisoning in children 5: rare and dangerous poisons.	2002 Nov	12390912
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
Re-evaluation of lisuride pharmacology: 5-hydroxytryptamine1A receptor-mediated behavioral effects overlap its other properties in rats.	2002 Oct	12373423
[Hawaiian baby woodrose: (Psycho-) Pharmacological effects of the seeds of Argyreia nervosa. A case-orientated demonstration].	2002 Sep	12215884
A common oscillator for perceptual rivalries?	2003	12729381
[Clinical methods in evolutional physiology].	2003 Jan-Feb	12739261
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
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
Creation, expression, and characterization of a constitutively active mutant of the human serotonin 5-HT6 receptor.	2003 Mar	12494404
Dynamic changes in prefrontal cortex gene expression following lysergic acid diethylamide administration.	2003 Mar 17	12654518
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

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 `Fri Dec 15 15:09:44 GMT 2023` Edited by `admin` on `Fri Dec 15 15:09:44 GMT 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