Lysergid

LSD · LSA · Ergine · lsd-25 · LYSERGIDE · Lysergamide · Cubes · D-LSD

Identifikatoren & physikalische Daten

CAS No.	50-37-3
Summenformel	C20H25N3O
Durchschnittliche Molmasse	323,4 g/mol
Monoisotopische Masse	323,19976242 g/mol
SMILES	CCN(CC)C(=O)[C@@H]1C=C2c3cccc4[nH]cc(c34)C[C@H]2N(C)C1
InChIKey	VAYOSLLFUXYJDT-RDTXWAMCSA-N
PubChem CID	5761
ChEMBL	CHEMBL263881
ChEBI	CHEBI:6605
EC No.	200-033-2
DTXSID	DTXSID1023231
Lokaler Name	Lysergid

Chemische & physikalische Eigenschaften

XLogP	3
Polarare Oberfläche (TPSA)	39,3
H-Brücken-Donoren	1
H-Brücken-Akzeptoren	2
Frei drehbare Bindungen	3
Schwere Atome	24
Formalladung	0
Komplexität	527
Arzneimittel	DEA NFLIS-Drug Category -> PsychedelicsDEA Schedule I Controlled Substance -> Hallucinogenic substancesPharmaceuticals -> Illicit drugsPharmaceuticals -> Synthetic Cannabinoids or Psychoactive CompoundsPharmaceuticals -> Listed in ZINC15
LogP (Verteilungskoeffizient)	log Kow = 2.95
Geruch	Odorless
Geschmack	Tasteless
Color/Form	Pointed prisms from benzeneColorless
Löslichkeit	Water solubleChloroform (Slightly), DMSO (Slightly), Methanol (Slightly, Heated)
Decomposition	When heated to decomposition it emits toxic fumes of /nitrogen oxides/.
Schmelzpunkt	176 to 185 °F (NTP, 1992)82 °CCrystals (with 1-2 molecules of water) in plates from water. MP: 240 °C (decomposes). Amphotericmoderately soluble in pyridineslightly soluble in water and neutral organic soventssoluble in alkaline and acid solutions /Lysergic acid/91-93C
Optical Rotation	Specific optical rotation: 17 deg at 20 °C/C (c = 0.5 g in 100 mL pyridine)
Physical Description	Prismatic crystals (from benzene). Tasteless and odorless. A hallucinogen.
Stability/Shelf Life	Stable under recommended storage conditions.LSD ... decomposes in light and at high temperatures.
Dissociation Constants	7.8
Siedepunkt	461.9°C (rough estimate)
Dichte	1.1021 (rough estimate)
Brechungsindex	1.6200 (estimate)
Flammpunkt	2℃
Lagerbedingungen	−20°C
pKa (Säurekonstante)	pKa 7.5 (Uncertain)
Aggregatzustand	Solid
Farbe	Pale Brown to Brown
Henry-Konstante	6.6×1010 mol/(m3Pa) at 25℃, HSDB (2015)
Stabilität	Stable. Incompatible with strong oxidizing agents.
EPA chemische Informationen	Lysergide (50-37-3)

Sicherheit & Vorschriften

GHS-Einstufung	DangerH300 (97.6%): Fatal if swallowed [Danger Acute toxicity, oral]P203, P260, P262, P264, P270, P271, P280, P284, P301+P316, P302+P352, P304+P340, P316, P318, P320, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 42 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]
Regulatorische Informationen	DEA schedule I controlled substance
DOT-Kennzeichnung	Poison
Brandgefahren	Flash point data for this chemical are not availablehowever it is probably combustible. (NTP, 1992)
Gesundheitsgefahren	SYMPTOMS: Symptoms of exposure to this chemical are euphoria, hallucinations, distorted perception, excitement, and anorexia. It can cause central nervous system effects, tachycardia, muscular weakness, increased body temperature, wavelike recurrences of perceptual changes, difficulty in locating the source of sound, hypervigilant, withdrawn or may alternate between states, fear of fragmentation or disintegration of the self, prolonged afterimages, overlapping of present and preceding perceptions, synesthesias, colors are heard and sounds may be seen, subjective time is seriously altered and moods may be labile. In addition, it can cause tremor, piloerection, pupillary dilatation, salivation, hyperreflexia, ataxia, and spastic paresis. It can cause vomiting. Other symptoms are hypertension and hypotension, coma, prolonged psychotic state, psychopathic personality disorders, increased homicidal and suicidal risk, and possible chromosome injury. Hyperexcitability and convulsions can also be symptoms of exposure to this chemical. This compound can inhibit the firing of the raphe neurons. It can also be habit forming.
FDA-Anforderungen	Schedule I shall consist of the drugs and other substances, by whatever official name, common or usual name, chemical name, or brand name designated, listed in this section. Each drug or substance has been assigned the DEA Controlled Substances Code Number set forth opposite it. ... Unless specifically excepted or unless listed in another schedule, any material, compound, mixture, or preparation, which contains any quantity of the following hallucinogenic substances, or which contains any of its salts, isomers, and salts of isomers whenever the existence of such salts, isomers, and salts of isomers is possible within the specific chemical designation (for purposes of this paragraph only, the term "isomer" includes the optical, position and geometric isomers). Lysergic acid diethylamide (DEA Code Number: 7315) is included on this list.

Anwendungen & Verwendung

Beschreibung

Lysergic acid diethylamide (LSD) is synthetically derived from the fungus, Claviceps purpuria. Several isomers of this compound exist, although only the D-isomer is considered active. LSD was first synthesized by Albert Hofmann in 1938 in a search for an analeptic drug. After finding its psychogenic activity, it was marketed by Sandoz laboratories under the name Delysid. It was also reportedly used by the Central Intelligence Agency as a tool for interrogation. Due to its potential for ‘bad trips,’ ‘flashbacks,’ and potential risk for brain injury, LSD was banned federally in 1966 and is currently only used illicitly. LSD is chemically similar to other naturally occurring lysergamides found in multiple species of morning glory.

Verwenden

LSD is obtained by partial synthesis fromD-lysergic acid. It is also produced bymicrobial reaction of Claviceps paspali overthe hydroxylethylamide. It is a well-knownhallucinogen and a drug of abuse, listed asa controlled substance in the U.S. Code ofFederal Regulations (Title 21, Part 1308.11,1987). It is used as an antagonist to serotoninand in the study and treatment of mentaldisorders.