(2'S,4'S)-(+)-9,10-didehydro-6-methylergoline-8β-(cis-2,4-dimethylazetidide) | 470666-31-0

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 麦角林及其衍生物
• 英文名称: (2'S,4'S)-(+)-9,10-didehydro-6-methylergoline-8β-(cis-2,4-dimethylazetidide)
• 英文别名: Lysergic acid 2,4-dimethylazetidide；[(6aR,9R)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinolin-9-yl]-[(2S,4S)-2,4-dimethylazetidin-1-yl]methanone
• CAS: 470666-31-0
• 化学式: C₂₁H₂₅N₃O
• 分子量: 335.449
• InChiKey: DUKNIHFTDAXJON-CTQRGLTFSA-N

物化性质

• 沸点：
  565.1±50.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  39.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  S,S-trans-2,4-dimethylazetidine 、 麦角酸 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (2'S,4'S)-(+)-9,10-didehydro-6-methylergoline-8β-(cis-2,4-dimethylazetidide)
  参考文献：
  名称：

  Lysergamides of Isomeric 2,4-Dimethylazetidines Map the Binding Orientation of the Diethylamide Moiety in the Potent Hallucinogenic Agent N,N-Diethyllysergamide (LSD)

  摘要：

  Lysergic acid amides were prepared from (R,R)-(-)-, (S,S)-(+)-, and cis-2,4-dimethyl azetidine. The dimethylazetidine moiety is considered here to be a rigid analogue of diethylamine, and thus, the target compounds are all conformationally constrained analogues of the potent hallucinogenic agent, N,N-diethyllysergamide, LSD-25. Pharmacological evaluation showed that (S,S)-(+)-2,4-dimethylazetidine gave a lysergamide with the highest LSD-like behavioral activity in the rat two lever drug discrimination model that was slightly more potent than LSD itself. This same diastereomer also had the highest affinity. and functional potency at the rat serotonin 5-HT2A receptor, the presumed target for hallucinogenic agents, and a receptor affinity profile in a panel of screens that was most similar to that of LSD itself. Both cis- and the (R,R)-trans-dimethylazetidines gave lysergamides that were less potent in all relevant assays. The finding that the S,S-dimethylazetidine gave a lysergamide with pharmacology most similar to LSD indicates that the N,N-diethyl groups of LSD optimally bind when they are oriented in a conformation distinct from that observed in the solid state by X-ray crystallography. The incorporation of isomeric dialkylazetidines into other biologically active molecules may be a useful strategy to model the active conformations of dialkylamines and dialkylamides.

  DOI：

  10.1021/jm020153s

文献信息

• COMPOSITIONS COMPRISING A PSILOCYBIN DERIVATIVE AND A CANNABINOID
  申请人：CaaMTech, LLC

  公开号：US20190142851A1

  公开（公告）日：2019-05-16

  This disclosure pertains to new compositions and methods comprising a psilocybin derivative. In one embodiment, the compositions disclosed herein are used for a method of regulating a neurotransmitter receptor, e.g., a serotonin receptor. In one embodiment, the compositions disclosed herein comprise purified compounds, e.g., a purified psilocybin derivative, a purified cannabinoid, or purified terpene.
• COMPOSITIONS COMPRISING A SEROTONERGIC TRYPTAMINE COMPOUND
  申请人：CAAMTECH, INC.

  公开号：US20210346346A1

  公开（公告）日：2021-11-11

  Disclosed herein are compositions comprising a serotonergic tryptamine compound, combinations thereof, and methods of using them for treating and preventing a variety of human conditions. In one embodiment, disclosed herein are new compositions and methods which comprise a therapeutically effective amount of a first purified psilocybin derivative and a therapeutically effective amount of a second compound. The second compound is selected from the group consisting of a second purified psilocybin derivative, a purified terpene, a serotonergic drug, an adrenergic drug, a dopaminergic drug, a purified erinacine, and a purified hericenone.
• [EN] METHODS FOR TREATING DISEASES<br/>[FR] MÉTHODES DE TRAITEMENT DE MALADIES
  申请人：CHILDRENS HOSPITAL MED CT

  公开号：WO2021097003A1

  公开（公告）日：2021-05-20

  Some embodiments of the invention include methods for treating an animal for a disease comprising one or more administrations of one or more compositions comprising (a) a TNF signaling inhibitor, (b) a CD40 inhibitor, a FAS signaling inhibitor, or both, and (c) optionally, a caspase 8 inhibitor. Other embodiments include methods for treating the disease comprising one or more administrations of one or more compositions comprising (a) the TNF signaling inhibitor and (b) the CD40 inhibitor. Certain embodiments include methods for treating the disease comprising one or more administrations of one or more compositions comprising (a) the TNF signaling inhibitor, (b) the FAS signaling inhibitor, and (c) optionally, the caspase 8 inhibitor. Still other embodiments include methods for treating a human for autoimmune disease, T cell mediated autoimmune disease, IL-1β mediated autoimmune disease, or cytokine release syndrome. Additional embodiments of the invention are also discussed herein.
• [EN] COMPOSITIONS AND METHODS FOR TREATING MIGRAINE<br/>[FR] COMPOSITIONS ET MÉTHODES DE TRAITEMENT DE LA MIGRAINE
  申请人：[en]WESANA HEALTH INC.

  公开号：WO2022115798A2

  公开（公告）日：2022-06-02

  As described below, the present disclosure features compositions containing a cannabidiol (CBD) and/or psilocybin, optionally in combination with a mushroom blend. The present disclosure also features methods for treating or preventing migraine, or symptoms thereof, with a cannabidiol and/or psilocybin, optionally in combination with a mushroom blend. The present disclosure also features compositions and methods of using psilocybin in combination with a neurotransmitter activity modulator for the treatment of neurological conditions (e.g., migraine), or symptoms thereof (e.g., anxiety or depression).
• Lysergamides of Isomeric 2,4-Dimethylazetidines Map the Binding Orientation of the Diethylamide Moiety in the Potent Hallucinogenic Agent <i>N</i>,<i>N</i>-Diethyllysergamide (LSD)
  作者：David E. Nichols、Stewart Frescas、Danuta Marona-Lewicka、Deborah M. Kurrasch-Orbaugh

  DOI：10.1021/jm020153s

  日期：2002.9.1

  Lysergic acid amides were prepared from (R,R)-(-)-, (S,S)-(+)-, and cis-2,4-dimethyl azetidine. The dimethylazetidine moiety is considered here to be a rigid analogue of diethylamine, and thus, the target compounds are all conformationally constrained analogues of the potent hallucinogenic agent, N,N-diethyllysergamide, LSD-25. Pharmacological evaluation showed that (S,S)-(+)-2,4-dimethylazetidine gave a lysergamide with the highest LSD-like behavioral activity in the rat two lever drug discrimination model that was slightly more potent than LSD itself. This same diastereomer also had the highest affinity. and functional potency at the rat serotonin 5-HT2A receptor, the presumed target for hallucinogenic agents, and a receptor affinity profile in a panel of screens that was most similar to that of LSD itself. Both cis- and the (R,R)-trans-dimethylazetidines gave lysergamides that were less potent in all relevant assays. The finding that the S,S-dimethylazetidine gave a lysergamide with pharmacology most similar to LSD indicates that the N,N-diethyl groups of LSD optimally bind when they are oriented in a conformation distinct from that observed in the solid state by X-ray crystallography. The incorporation of isomeric dialkylazetidines into other biologically active molecules may be a useful strategy to model the active conformations of dialkylamines and dialkylamides.