(4R,7R)-N,N-diethyl-6-methyl-6,11-diazatetracyclo[7.6.1.02,7.012,16]hexadeca-1(15),2,9,12(16),13-pentaene-4-carboxamide

• ChemBase编号: 4373
• 分子式: C20H25N3O
• 平均质量: 323.432
• 单一同位素质量: 323.19976244
• SMILES: O=C(N(CC)CC)[C@H]1CN([C@H]2C(=C1)c1c3c(C2)c[nH]c3ccc1)C
• Canonical SMILES: CCN(C(=O)[C@H]1CN(C)[C@H]2C(=C1)c1cccc3c1c(C2)c[nH]3)CC
• InChI: InChI=1S/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
• InChIKey: VAYOSLLFUXYJDT-RDTXWAMCSA-N

名称和登记号

名称

• IUPAC标准名: (4R,7R)-N,N-diethyl-6-methyl-6,11-diazatetracyclo[7.6.1.0^2,^7.0^1^2,^1^6]hexadeca-1(15),2,9,12(16),13-pentaene-4-carboxamide; (4R,7R)-N,N-diethyl-6-methyl-6,11-diazatetracyclo[7.6.1.0^2,^7.0^1^2,^1^6]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide; (4R,7R)-N,N-diethyl-6-methyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide
• IUPAC传统名: (4R,7R)-N,N-diethyl-6-methyl-6,11-diazatetracyclo[7.6.1.0^2,^7.0^1^2,^1^6]hexadeca-1(15),2,9,12(16),13-pentaene-4-carboxamide; lysergic acid diethylamide
• 别名: (8β)-9,10-Didehydro-N,N-diethyl-6-methylergoline-8-carboxamide; Lysergic Acid Diethylamide; Lysergide; Lysergic acid diethylamide; LSD-25,; lysergidD; ; D-lysergic acid diethyl amidD; ; ''N'',''N''- diethyl- D- lysergamide; N,N-Diethyl-6-methyl-9,10-didehydroergoline-8-carboxamide; n,n-diethyl-(+)-lysergamide; Lysergidum [inn-latin]; Lysergide; Diethylamid kyseliny lysergove [czech]; Dextrolysergic acid diethylamide; Delysid; D-lysergic acid n,n-diethylamide; D-lysergic acid diethylamide; D-lysergic acid dethylamide; D-LSD-25; D-LSD; Cupcakes; Cubes; Contact lens; Coffeinum; Clearlight; Chocolate chips; Chief; Cherry top; California sunshine; Brown dots; Blue star; Blue mist; Microdots; Mellow yellow; Mean green; Lysergic acid diethylamide-25; Lysergic acid amide; Lysergaure diethylamid; Lysergamide; Lysergamid; Lucy in the sky with diamonds; Heavenly blue; Greenies; Gelatin chips; Frogs; Flats; Fifty; Ergine; Domes; Lysergic Acid Diethylamide; LSD; LSD-25; (+)-LSD; (+)-lysergic acid diethylamide; 9,10-Didehydro-N,N-diethyl-6-methylergoline-8b-carboxamide; Acid; Barrels; Bart simpson; Bartman; Beast; Big f; Blotter acid; Blue acid; Blue cheer; ZEN; Yellows; Window pane; White light; Wedges; Wedding bells; Ubergluben; Trippers; TMA; The hawk; TABS; Sunshine; Sugar lump; Sugar; Strawberry fields; Spoonies; Scapes; Royal blue; Purple microdot; Purple haze; Pearly gates; Paper acid; Owsley; Orange wedges; Orange sunshine; Orange mushroom; N,n-diethyllysergamide; N,n-diethyl-d-lysergamide; acid

登记号

• CAS号: 50-37-3; 89-77-0
• EC号: 200-033-2
• MDL号: MFCD00135795
• PubChem SID: 46506397; 24896390; 160967805
• PubChem CID: 5761
• CHEBI ID: 6605
• CHEMBL: 263881
• Chemspider ID: 5558
• DrugBank ID: DB04829
• IUPHAR配体索引: 17
• 美国药典/FDA物质标识码: 8NA5SWF92O
• 维基百科标题: Lysergic_acid_diethylamide

理论计算性质

JChem

• Acid pKa: 17.018362
• 质子受体: 2
• 质子供体: 1
• LogD (pH = 5.5): -0.15770875
• LogD (pH = 7.4): 1.6029848
• Log P: 2.281515
• 摩尔折射率: 98.7347 cm^3
• 极化性: 38.704967 Å^3
• 极化表面积: 39.34 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 3.3
• LOG S: -3.08
• 溶解度: 2.70e-01 g/l

分子性质

理化性质

• 溶解度: Chloroform; Methanol; Pyridine
• 外观: Brown Solid
• 熔点: 80-85 °C (176-185°F); 91-93°C
• 疏水性(logP): 2.95 [HANSCH,C ET AL. (1995)]

安全信息

• 保存条件: Controlled Substance, -20°C Freezer
• RTECS编号: KE4100000
• 欧盟危险性物质标志: 剧毒(Highly toxic) (T+)
• 联合国危险货物编号: 2811
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 2
• 危险公开号: 26/27/28-40
• 安全公开号: 22-28-36-45
• GHS危险品标识: GHS06; GHS08
• GHS警示词: Danger
• GHS危险声明: H300-H310-H330-H351
• GHS警示性声明: P260-P264-P280-P284-P302 + P350-P310
• 个人保护装置: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 2
• 毒品管制信息: USDEA Schedule I; Home Office Schedule 1; stupéfiant; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada
• 保存温度: -20°C

药理学性质

• 给药途径: Oral, Intravenous, Ocular, Intramuscular
• 依赖倾向: Very low
• 排泄: Renal
• 半衰期: 3–5 hours
• 代谢: Hepatic
• 法定药品分级: CD (UK); Schedule 9 (Australia); Schedule I (US); Schedule III (Canada)
• 妊娠期药物分类: C (US)
• 相关基因信息: human ... DRD2(1813), HTR1A(3350), HTR2A(3356), HTR2C(3358), HTR6(3362)rat ... Htr1a(24473), Htr2a(29595), Htr2c(25187), Htr7(65032)

产品相关信息

• 纯度: 97%

详细说明

DrugBank - DB04829

• Drug Groups: illicit; withdrawn
• Description: Debate continues over the nature and causes of chronic flashbacks. Explanations in terms of LSD physically remaining in the body for months or years after consumption have been discounted by experimental evidence. Some say HPPD is a manifestation of post-traumatic stress disorder, not related to the direct action of LSD on brain chemistry, and varies according to the susceptibility of the individual to the disorder. Many emotionally intense experiences can lead to flashbacks when a person is reminded acutely of the original experience. However, not all published case reports of chronic flashbacks appear to describe an anxious hyper-vigilant state reminiscent of post-traumatic stress disorder.
• Toxicity: Estimates for the lethal dosage (LD50) of LSD range from 200 μg/kg to more than 1 mg/kg of human body mass, though most sources report that there are no known human cases of such an overdose.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• Half Life: 3 hours
• References: GREINER T, BURCH NR, EDELBERG R: Psychopathology and psychophysiology of minimal LSD-25 dosage; a preliminary dosage-response spectrum. AMA Arch Neurol Psychiatry. 1958 Feb;79(2):208-10. [Pubmed] ; AGHAJANIAN GK, BING OH: PERSISTENCE OF LYSERGIC ACID DIETHYLAMIDE IN THE PLASMA OF HUMAN SUBJECTS. Clin Pharmacol Ther. 1964 Sep-Oct;5:611-4. [Pubmed] ; Papac DI, Foltz RL: Measurement of lysergic acid diethylamide (LSD) in human plasma by gas chromatography/negative ion chemical ionization mass spectrometry. J Anal Toxicol. 1990 May-Jun;14(3):189-90. [Pubmed] ; Nichols DE: Hallucinogens. Pharmacol Ther. 2004 Feb;101(2):131-81. [Pubmed] ; Jacobs BL, Heym J, Rasmussen K: Raphe neurons: firing rate correlates with size of drug response. Eur J Pharmacol. 1983 Jun 3;90(2-3):275-8. [Pubmed]
• External Links: Wikipedia

Sigma Aldrich - L7007

Biochem/physiol Actions
Potent hallucinogen; non-selective serotonin receptor agonist.

Toronto Research Chemicals - L488010

Potent hallucinogen; non-selective serotonin receptor agonist. Has been used experimentally as adjunct in study and treatment of mental disorders.Controlled substance.

参考文献

• GREINER T, BURCH NR, EDELBERG R: Psychopathology and psychophysiology of minimal LSD-25 dosage; a preliminary dosage-response spectrum. AMA Arch Neurol Psychiatry. 1958 Feb;79(2):208-10. Pubmed
• AGHAJANIAN GK, BING OH: PERSISTENCE OF LYSERGIC ACID DIETHYLAMIDE IN THE PLASMA OF HUMAN SUBJECTS. Clin Pharmacol Ther. 1964 Sep-Oct;5:611-4. Pubmed
• Papac DI, Foltz RL: Measurement of lysergic acid diethylamide (LSD) in human plasma by gas chromatography/negative ion chemical ionization mass spectrometry. J Anal Toxicol. 1990 May-Jun;14(3):189-90. Pubmed
• Jacobs BL, Heym J, Rasmussen K: Raphe neurons: firing rate correlates with size of drug response. Eur J Pharmacol. 1983 Jun 3;90(2-3):275-8. Pubmed
• Nichols DE: Hallucinogens. Pharmacol Ther. 2004 Feb;101(2):131-81. Pubmed
• Hoffer, et al.: Clin. Pharmacol. Ther., 6, 183 (1965)
• Keller, U., et al.: Biochemistry, 27, 6164 (1965)
• Mey, G., et al.: Mol. Microbiol., 46, 305 (1965)
• Steiner, U., et al.: Planta, 224, 533 (1965)