Journal: Journal of the American Society for Mass Spectrometry

Article Title: Investigating the Protonated Cannabinoid Dimer Detected in the Forensic Analysis of Cannabis by DART-MS: A Combined Mass Spectrometry and Computational Study

doi: 10.1021/jasms.5c00433

Figure Lengend Snippet: DART mass spectra of marijuana (15%w/w THC concentration) and hemp (0.07%w/w THC concentration) flowers; Δ 8 -THC, Δ 9 -THC, CBD, CBC, and CBT solutions; and a Δ 8 -THC + Δ 9 -THC + CBD + CBC + CBT mixture. Peaks at nominal m / z 315 represent [M + H] + peaks, while the peaks detected at m / z 629 indicate the presence of proton-bound cannabinoid dimers [2M + H] + .

Article Snippet: Δ 8 -THC, Δ 9 -THC, CBD, CBC, and CBT cannabinoid certified reference standards in methanol were purchased from Cayman Chemical (Ann Arbor, MI, USA).

Techniques: Concentration Assay

Journal: Journal of the American Society for Mass Spectrometry

Article Title: Investigating the Protonated Cannabinoid Dimer Detected in the Forensic Analysis of Cannabis by DART-MS: A Combined Mass Spectrometry and Computational Study

doi: 10.1021/jasms.5c00433

Figure Lengend Snippet: M06–2X/6–311++G­(2d,2p) level optimized geometries of CBD, CBC, Δ 9 -THC, Δ 8 -THC, and CBT. The gray, white, and red colors represent carbon, hydrogen, and oxygen atoms, respectively.

Article Snippet: Δ 8 -THC, Δ 9 -THC, CBD, CBC, and CBT cannabinoid certified reference standards in methanol were purchased from Cayman Chemical (Ann Arbor, MI, USA).

Techniques:

Journal: Journal of the American Society for Mass Spectrometry

Article Title: Investigating the Protonated Cannabinoid Dimer Detected in the Forensic Analysis of Cannabis by DART-MS: A Combined Mass Spectrometry and Computational Study

doi: 10.1021/jasms.5c00433

Figure Lengend Snippet: Three most stable proton-bound homodimer structures of CBD and Δ 9 -THC optimized at the M06–2X/6–311++G­(2d,2p) level of theory: (a) protonated CBD interacting with neutral CBD; (b) protonated Δ 9 -THC interacting with the −OH group of neutral Δ 9 -THC; and (c) protonated Δ 9 -THC interacting with the O atom of the pyran ring in neutral Δ 9 -THC. Bond lengths are given in Å. Binding energies (B.E.) were calculated at the M06–2X/6–311++G­(3df,3pd)//M06–2X/6–311++G­(2d,2p) level. Carbon, hydrogen, and oxygen atoms are shown in gray, white, and red, respectively.

Article Snippet: Δ 8 -THC, Δ 9 -THC, CBD, CBC, and CBT cannabinoid certified reference standards in methanol were purchased from Cayman Chemical (Ann Arbor, MI, USA).

Techniques: Binding Assay

Journal: Journal of the American Society for Mass Spectrometry

Article Title: Investigating the Protonated Cannabinoid Dimer Detected in the Forensic Analysis of Cannabis by DART-MS: A Combined Mass Spectrometry and Computational Study

doi: 10.1021/jasms.5c00433

Figure Lengend Snippet: Three most stable proton-bound heterodimer structures of CBD and Δ 9 -THC optimized at the M06–2X/6–311++G­(2d,2p) level of theory: (a) protonated CBD interacting with the −OH moiety of neutral Δ 9 -THC; (b) protonated CBD interacting with the O atom of the pyran ring in neutral Δ 9 -THC; and (c) protonated Δ 9 -THC interacting with neutral CBD. Bond lengths are reported in Å. Binding energies (B.E.) were calculated at the M06–2X/6–311++G­(3df,3pd)//M06–2X/6–311++G­(2d,2p) level. Carbon, hydrogen, and oxygen atoms are represented in gray, white, and red, respectively.

Article Snippet: Δ 8 -THC, Δ 9 -THC, CBD, CBC, and CBT cannabinoid certified reference standards in methanol were purchased from Cayman Chemical (Ann Arbor, MI, USA).

Techniques: Binding Assay

Journal: Journal of the American Society for Mass Spectrometry

Article Title: Investigating the Protonated Cannabinoid Dimer Detected in the Forensic Analysis of Cannabis by DART-MS: A Combined Mass Spectrometry and Computational Study

doi: 10.1021/jasms.5c00433

Figure Lengend Snippet: Most stable structures of the proton-bound heterodimers of CBD and Δ 9 -THC with CBC, Δ 8 -THC, and CBT optimized at the M06–2X/6–311++G­(2d,2p) level: (a) protonated CBD interacting with the O atom of the pyran ring in neutral CBC, Δ 8 -THC, and CBT, respectively; (b) protonated Δ 9 -THC interacting with the O atom of the pyran ring in neutral CBC, Δ 8 -THC, and CBT, respectively. Bond lengths are reported in Å. Binding energies (B.E.) were calculated at the M06–2X/6–311++G­(3df,3pd)//M06–2X/6–311++G­(2d,2p) level. Carbon, hydrogen, and oxygen atoms are shown in gray, white, and red, respectively.

Article Snippet: Δ 8 -THC, Δ 9 -THC, CBD, CBC, and CBT cannabinoid certified reference standards in methanol were purchased from Cayman Chemical (Ann Arbor, MI, USA).

Techniques: Binding Assay

Journal: Journal of the American Society for Mass Spectrometry

Article Title: Investigating the Protonated Cannabinoid Dimer Detected in the Forensic Analysis of Cannabis by DART-MS: A Combined Mass Spectrometry and Computational Study

doi: 10.1021/jasms.5c00433

Figure Lengend Snippet: Most stable structures of the proton-bound heterodimers of CBC, Δ 8 -THC, and CBT optimized at the M06–2X/6–311++G­(2d,2p) level: (a) most stable structures of the proton-bound heterodimers of CBC with CBD, Δ 9 -THC, Δ 8 -THC, and CBT; (b) most stable structures of the proton-bound heterodimers of Δ 8 -THC with CBD, Δ 9 -THC, CBC, and CBT; and (c) most stable structures of the proton-bound heterodimers of CBT with CBD, Δ 9 -THC, CBC, and Δ 8 -THC. Bond lengths are reported in Å. Binding energies (B.E.) were calculated at the M06–2X/6–311++G­(3df,3pd)//M06–2X/6–311++G­(2d,2p) level. Carbon, hydrogen, and oxygen atoms are represented in gray, white, and red, respectively.

Article Snippet: Δ 8 -THC, Δ 9 -THC, CBD, CBC, and CBT cannabinoid certified reference standards in methanol were purchased from Cayman Chemical (Ann Arbor, MI, USA).

Techniques: Binding Assay

Journal: Journal of the American Society for Mass Spectrometry

Article Title: Investigating the Protonated Cannabinoid Dimer Detected in the Forensic Analysis of Cannabis by DART-MS: A Combined Mass Spectrometry and Computational Study

doi: 10.1021/jasms.5c00433

Figure Lengend Snippet: Relative concentrations of the major proton-bound homo- and heterodimers of CBD, Δ 9 -THC, CBC, Δ 8 -THC, and CBT over the temperature range of 50–800 K.

Article Snippet: Δ 8 -THC, Δ 9 -THC, CBD, CBC, and CBT cannabinoid certified reference standards in methanol were purchased from Cayman Chemical (Ann Arbor, MI, USA).

Techniques: