Kevin Richard C, Kovach Alexander L, Lefever Timothy W, Gamage Thomas F, Wiley Jenny L, McGregor Iain S, Thomas Brian F
School of Psychology, The University of Sydney, NSW, 2006, Australia.
RTI International, 3040 Cornwallis Road, Research Triangle Park, NC, 27709, USA.
Forensic Toxicol. 2019 Jan;37(1):17-26. doi: 10.1007/s11419-018-0430-0. Epub 2018 Jun 28.
The use of novel synthetic cannabinoids as intoxicants continues in spite of associated health risks. These compounds are typically smoked or vaporized, but many synthetic cannabinoids contain thermally labile chemical moieties. This study investigated the thermal stability six carboxamide-type synthetic cannabinoids (CUMYL-PICA, 5F-CUMYL-PICA, AMB-FUBINACA, MDMB-FUBINACA, NNEI, and MN-18) in order to characterise potential user exposure to thermolysis products.
Compounds were heated sequentially to 200, 400, 600 and 800 °C using a thermolysis probe, and the resultant thermolysis products were analysed via GC-MS. A secondary analysis quantified thermolytically generated cyanide via LC-MS/MS.
All six synthetic cannabinoids underwent thermal degradation when heated above 400 °C, and released a variety of potentially toxic products, including toluene, naphthalene, and 1-naphthalamine. Compound-specific degradants were tentatively identified together with a general degradative pathway for carboxamide-type synthetic cannabinoids, which proceeds via indole- or indazole-amide formation and subsequent dehydration to an indole- or indazole-carbonitrile. This degradative pathway culminated in the thermolytic liberation of cyanide, in amounts up to 27 μg per mg of starting material.
People who smoke carboxamide-type synthetic cannabinoids are likely to be exposed to range of potentially toxic thermal degradants, including cyanide. These degradants could have significant health impacts in human users.
尽管存在健康风险，但新型合成大麻素仍被用作毒品。这些化合物通常通过吸烟或汽化使用，但许多合成大麻素含有热不稳定的化学部分。本研究调查了六种羧酰胺型合成大麻素（CUMYL-PICA、5F-CUMYL-PICA、AMB-FUBINACA、MDMB-FUBINACA、NNEI和MN-18）的热稳定性，以确定使用者接触热解产物的可能性。
使用热解探针将化合物依次加热至200、400、600和800°C，通过气相色谱-质谱联用仪（GC-MS）分析所得热解产物。二次分析通过液相色谱-串联质谱联用仪（LC-MS/MS）对热解产生的氰化物进行定量。
当加热到400°C以上时，所有六种合成大麻素都会发生热降解，并释放出多种潜在有毒产物，包括甲苯、萘和1-萘胺。初步鉴定了化合物特异性降解产物以及羧酰胺型合成大麻素的一般降解途径，该途径通过吲哚或吲唑酰胺的形成以及随后脱水形成吲哚或吲唑腈。这条降解途径最终导致氰化物的热解释放，每毫克起始原料中氰化物含量高达27μg。
吸食羧酰胺型合成大麻素的人可能会接触到一系列潜在有毒的热降解产物，包括氰化物。这些降解产物可能会对使用者的健康产生重大影响。
