50-37-3 Usage
Description
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.
Chemical Properties
crystalline solid
History
lysergic acid diethylamide(LSD) is a hallucinogenic drug that was first synthesized a Swiss scientist in the 1930s. During the Cold War, the CIA conducted clandestine experiments with LSD (and other drugs) for mind control, information gathering and other purposes. Over time, the drug became a symbol of the 1960s counterculture, eventually joining other hallucinogenic and recreational drugs at rave parties.
Uses
Different sources of media describe the Uses of 50-37-3 differently. You can refer to the following data:
1. 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.
2. Labelled Lysergide (L488010)
3. Potent hallucinogen; non-selective serotonin receptor agonist. Has been used experimentally as adjunct in study and treatment of mental disorders.
Controlled substance.
Definition
ChEBI: An ergoline alkaloid arising from formal condensation of lysergic acid with diethylamine.
General Description
Prismatic crystals (from benzene). Tasteless and odorless. A hallucinogen.
Reactivity Profile
An amide. Organic amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx).
Health Hazard
LSD is a strong psychedelic agent. Theeffects in human are excitement, euphoria,hallucinations, and distorted perceptions.It alters the thinking process, producingillusions and loss of contact with reality.In humans, a dose (intramuscular)of 0.7–0.9 mg/kg or an oral dose of2.5–3.0 mg/kg may produce the effectsabove. Other symptoms may include nausea,vomiting, dilation of pupils, restlessness, andperipheral vascoconstriction. However, thereis no reported case of overdose death. In rabbits,somnolence, ataxia, and an increase inbody temperature were the symptoms notedat the LD50 (intravenous) doses at 0.3 mg/kg.LD50 value, intravenous (mice): 46 mg/kgLD50 value, subcutaneous (guinea pigs):16 mg/kg.
Fire Hazard
Flash point data for LSD are not available; however LSD is probably combustible.
Safety Profile
Poison by ingestion,
subcutaneous, intraperitoneal, and
intravenous routes. Mutation data reported.
Human systemic effects by ingestion and
intramuscular routes: euphoria,
hallucinations, distorted perceptions,
excitement, anorexia, nausea and vomiting.
An experimental teratogen. Other
experimental reproductive effects. Mutation
data reported. A much-abused hallucinogen.
A federally regulated substance. When
heated to decomposition it emits toxic
fumes of NOx
Environmental Fate
LSD may exist in the air or soil. In the air, LSD may be
susceptible to photochemical reactions with subsequently induced radical analogs. Photolysis and oxidative degradation
may occur with an airborne half-life of 18 min. LSD’s pKa of 7.8
will have a meaningful percentage of the drug in the cationic
form allowing it to interact with soil.
Toxicity evaluation
LSD’s mechanism of action is not completely understood.
LSD’s hallucinogenic effects are secondary to its ability to
increase central serotonin activity. LSD also stimulates both
D1 and D2 dopamine receptors.
Check Digit Verification of cas no
The CAS Registry Mumber 50-37-3 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 0 respectively; the second part has 2 digits, 3 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 50-37:
(4*5)+(3*0)+(2*3)+(1*7)=33
33 % 10 = 3
So 50-37-3 is a valid CAS Registry Number.
InChI:InChI=1/C20H25N3O/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/h6-9,11,14,18,21H,4-5,10,12H2,1-3H3/t14-,18-/m1/s1
50-37-3Relevant articles and documents
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Stoll et al.
, p. 820,823 (1954)
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Reagents for lysergic acid diethylamide immunoassay
-
, (2008/06/13)
The present invention provides hapten derivatives that are useful for the preparation of antigens, antibodies and reagents having superior performance characteristics for use in immunoassays for the detection of LSD and nor-LSD. In the present invention the LSD nucleus is derivatized out of the indole nitrogen to form an aminoalkyl derivative. Derivatives have also been synthesized out of the piperidine nitrogen of the LSD nucleus. The resulting haptens can then be further modified at these functionalized positions for linking to appropriate antigenic or labelling groups to provide reagents for LSD immunoassays having excellent sensitivity and selectivity for both LSD and nor-LSD.
Studies on Lysergic Acid Diethylamide and Related Compounds. Part 8. Structural Identification of New Metabolites of Lysergic Acid Diethylamide obtained by Microbial Transformation using Streptomyces roseochromogenes
Ishii, Hisashi,Niwaguchi, Tetsukichi,Nakahara, Yuji,Hayashi, Makoto
, p. 902 - 905 (2007/10/02)
Microbial transformation of lysergic acid diethylamide (1) by Streptomyces roseochromogenes gave a known product, lysergic acid ethylamide (5), and two new ones.The structures of these new metabolites have been chemically established as lysergic acid ethylvinylamide (7) and lysergic acid ethyl-2-hydroxyethylamide (8).
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