1345973-49-0

Basic information

• Product Name: AB-001
• Synonyms: AB-001;(1-Pentyl-1H-indol-3-yl)tricyclo[3.3.1.1(3,7)]dec-1-ylmethanone;1-Pentyl-3-(adamant-1-oyl)indole;1-adamantyl-(1-pentylindol-3-yl)methanone
• CAS NO: 1345973-49-0
• Molecular Formula: C₂₄H₃₁NO
• Molecular Weight: 349.50904
• EINECS: -0
• Product Categories: Research Chemical
• Mol File: 1345973-49-0.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 501.092 °C at 760 mmHg
• Flash Point: 256.852 °C
• Appearance: /
• Density: 1.21
• CAS DataBase Reference: AB-001(CAS DataBase Reference)
• NIST Chemistry Reference: AB-001(1345973-49-0)
• EPA Substance Registry System: AB-001(1345973-49-0)

Safety Data

• Hazardous Substances Data: 1345973-49-0(Hazardous Substances Data)

Usage

Uses

AB-001 is an ingredient found in synthetic cannabis and acts as a full agonist at cannabinoid receptors however, it has a relative weak potency compared to other ingredients in synthetic cannabis. Synthetic Cannabinoids

Synthetic route

1-pentyl-1H-indole (59529-21-4) + 1-Adamantanecarbonyl chloride (2094-72-6) → 1-pentyl-N-tricyclo[3.3.1.1]dec-1-yl-1H-indole-3-carboxamide (1345973-49-0)

Conditions	Yield
Stage #1: 1-pentyl-1H-indole With dimethylaluminum chloride In hexane; dichloromethane at 0℃; Inert atmosphere; Stage #2: 1-Adamantanecarbonyl chloride In hexane; dichloromethane for 2h; Inert atmosphere;	86%

indole (120-72-9) → 1-pentyl-N-tricyclo[3.3.1.1]dec-1-yl-1H-indole-3-carboxamide (1345973-49-0)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.17 h / 20 °C / Inert atmosphere 1.2: 0 - 20 °C / Inert atmosphere 2.1: dimethylaluminum chloride / dichloromethane; hexane / 0 °C / Inert atmosphere 2.2: 2 h / Inert atmosphere View Scheme

1-Bromopentane (110-53-2) → 1-pentyl-N-tricyclo[3.3.1.1]dec-1-yl-1H-indole-3-carboxamide (1345973-49-0)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.17 h / 20 °C / Inert atmosphere 1.2: 0 - 20 °C / Inert atmosphere 2.1: dimethylaluminum chloride / dichloromethane; hexane / 0 °C / Inert atmosphere 2.2: 2 h / Inert atmosphere View Scheme

1-Adamantanecarboxylic acid (828-51-3) → 1-pentyl-N-tricyclo[3.3.1.1]dec-1-yl-1H-indole-3-carboxamide (1345973-49-0)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 1 h / Inert atmosphere 2.1: dimethylaluminum chloride / dichloromethane; hexane / 0 °C / Inert atmosphere 2.2: 2 h / Inert atmosphere View Scheme

Upstream product

• 120-72-9 indole 
• 59529-21-4 1-pentyl-1H-indole 
• 2094-72-6 1-Adamantanecarbonyl chloride 
• 110-53-2 1-Bromopentane 
• 828-51-3 1-Adamantanecarboxylic acid 

Relevant articles and documents

The synthesis and pharmacological evaluation of adamantane-derived indoles: Cannabimimetic drugs of abuse

Two novel adamantane derivatives, adamantan-1-yl(1-pentyl-1H-indol-3-yl) methanone (AB-001) and N-(adamtan-1-yl)-1-pentyl-1H-indole-3-carboxamide (SDB-001), were recently identified as cannabimimetic indoles of abuse. Conflicting anecdotal reports of the psychoactivity of AB-001 in humans, and a complete dearth of information about the bioactivity of SDB-001, prompted the preparation of AB-001, SDB-001, and several analogues intended to explore preliminary structure-activity relationships within this class. This study sought to elucidate which structural features of AB-001, SDB-001, and their analogues govern the cannabimimetic potency of these chemotypes in vitro and in vivo. All compounds showed similar full agonist profiles at CB1 (EC50 = 16-43 nM) and CB2 (EC50 = 29-216 nM) receptors in vitro using a FLIPR membrane potential assay, with the exception of SDB-002, which demonstrated partial agonist activity at CB2 receptors. The activity of AB-001, AB-002, and SDB-001 in rats was compared to that of Δ9-tetrahydrocannabinol (Δ9-THC) and cannabimimetic indole JWH-018 using biotelemetry. SDB-001 dose-dependently induced hypothermia and reduced heart rate (maximal dose 10 mg/kg) with potency comparable to that of Δ9-tetrahydrocannabinol (Δ9-THC, maximal dose 10 mg/kg), and lower than that of JWH-018 (maximal dose 3 mg/kg). Additionally, the changes in body temperature and heart rate affected by SDB-001 are of longer duration than those of Δ9-THC or JWH-018, suggesting a different pharmacokinetic profile. In contrast, AB-001, and its homologue, AB-002, did not produce significant hypothermic and bradycardic effects, even at relatively higher doses (up to 30 mg/kg), indicating greatly reduced potency compared to Δ9-THC, JWH-018, and SDB-001.