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N,N-Diethyllysergamide

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Name

N,N-Diethyllysergamide

EINECS 200-033-2
CAS No. 50-37-3 Density 1.216 g/cm3
PSA 39.34000 LogP 2.84390
Solubility N/A Melting Point 80 - 85 C
Formula C20H25N3O Boiling Point 541.279 °C at 760 mmHg
Molecular Weight 323.438 Flash Point 281.156 °C
Transport Information UN 2811 Appearance crystalline solid
Safety 22-28-36-45-33-24-16-7 Risk Codes 26/27/28-40-36/38-23/25
Molecular Structure Molecular Structure of 50-37-3 (Lysergide) Hazard Symbols VeryT+, ToxicT, FlammableF
Synonyms

Acid Diethylamide, Lysergic;Diethylamide, Lysergic Acid;LSD;LSD 25;LSD-25;Lysergic Acid Diethylamide;Lysergic Acid Diethylamide Tartrate;Lysergide

 

N,N-Diethyllysergamide Consensus Reports

EPA Genetic Toxicology Program.

N,N-Diethyllysergamide Specification

The systematic name of N,N-Diethyllysergamide is (8beta)-N,N-diethyl-6-methyl-9,10-didehydroergoline-8-carboxamide. With the CAS registry number 50-37-3, it is also named as Lysergic acid diethylamide. The classification codes are Central Nervous System Agents; Drug / Therapeutic Agent; Hallucinogens; Human Data; Mutation data; Neurotransmitter Agents; Psychotropic Drugs; Reproductive Effect; Serotonin Agents; Serotonin antagonists. It is crystalline solid which is an ergoline derivative and a chiral compound. When heated to decomposition it emits toxic fumes of NOx. So the storage environment should be well-ventilated, low-temperature and dry. Keep N,N-Diethyllysergamide separate from raw materials of food.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 2.71; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.765; (4)ACD/LogD (pH 7.4): 2.373; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 31.066; (7)ACD/KOC (pH 5.5): 8.051; (8)ACD/KOC (pH 7.4): 326.239; (9)#H bond acceptors: 4; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 39.34 Å2; (13)Index of Refraction: 1.652; (14)Molar Refractivity: 97.224 cm3; (15)Molar Volume: 266.033 cm3; (16)Surface Tension: 55.942 dyne/cm; (17)Enthalpy of Vaporization: 81.912 kJ/mol; (18)Vapour Pressure: 0 mmHg at 25°C; (19)Rotatable Bond Count: 3; (20)Tautomer Count: 2; (21)Exact Mass: 323.199762; (22)MonoIsotopic Mass: 323.199762; (23)Topological Polar Surface Area: 39.3; (24)Heavy Atom Count: 24.

Preparation of N,N-Diethyllysergamide: It is obtained by reacting diethylamine with an activated form of lysergic acid. Activating reagents include phosphoryl chloride and peptide coupling reagents. Lysergic acid is produced by alkaline hydrolysis of lysergamides like ergotamine, a substance derived from the ergot fungus on rye, or from ergine (lysergic acid amide, LSA), a compound that is found in morning glory (Ipomoea tricolor) and Hawaiian baby woodrose (Argyreia nervosa) seeds.

Uses of N,N-Diethyllysergamide: It is a semisynthetic psychedelic drug of the ergoline family. It has been used in psychiatry for its perceived therapeutic value, in the treatment of alcoholism, pain and cluster headache relief, for spiritual purposes, and to enhance creativity. It is also used mainly as an entheogen, recreational drug, and as an agent in psychedelic therapy.

When you are using this chemical, please be cautious about it as the following:
It is not only toxic by inhalation, in contact with skin and if swallowed, but also irritating to eyes and skin. Anf it has limited evidence of a carcinogenic effect. So people should not breathe dust and avoid contact with skin. After contact with skin, wash immediately with plenty of soap-suds. If you want to contact this product, you must wear suitable protective clothing. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 

People can use the following data to convert to the molecule structure. 
1. SMILES:CCN(CC)C(=O)[C@H]1CN([C@@H]2Cc3c[nH]c4c3c(ccc4)C2=C1)C
2. 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
3. InChIKey:VAYOSLLFUXYJDT-RDTXWAMCBY

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
bird - wild LD50 oral 1800ug/kg (1.8mg/kg)   Toxicology and Applied Pharmacology. Vol. 21, Pg. 315, 1972.
guinea pig LD50 subcutaneous 16mg/kg (16mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 137, Pg. 375, 1962.
human TDLo intramuscular 750ng/kg (0.00075mg/kg) BEHAVIORAL: EUPHORIA

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"
Psychopharmacologia Vol. 3, Pg. 219, 1962.
human TDLo oral 700ng/kg (0.0007mg/kg) BEHAVIORAL: EXCITEMENT Journal of Pharmacology and Experimental Therapeutics. Vol. 120, Pg. 340, 1957.
human TDLo oral 857ng/kg (0.000857mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BEHAVIORAL: ANOREXIA (HUMAN

GASTROINTESTINAL: NAUSEA OR VOMITING
Arzneimittel-Forschung. Drug Research. Vol. 16, Pg. 220, 1966.
 
human TDLo oral 2857ng/kg (0.002857mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 356, 1969.
mouse LD50 intraperitoneal 50mg/kg (50mg/kg)   National Technical Information Service. Vol. AD277-689,
mouse LD50 intravenous 46mg/kg (46mg/kg)   International Record of Medicine. Vol. 172, Pg. 702, 1959.
rabbit LD50 intravenous 300ug/kg (0.3mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA
Annals of the New York Academy of Sciences. Vol. 66, Pg. 668, 1957.
 
rat LD50 intravenous 16mg/kg (16mg/kg)   International Record of Medicine. Vol. 172, Pg. 702, 1959.