Methiopropamine is a methamphetamine structural analog in which the phenyl group has been replaced by thiophene. This compound’s physiological and toxicological effects have not been investigated. This item is designed for forensic and research purposes.
N-methyl-1-thiophen-2-ylpropan-2-amine;hydrochloride
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The title compound was prepared using an adaptation of the synthesis reported by Blicke et al.6 as an off-white crystalline powder (3.06 g, 14%) after recrystallization from ethanol–acetone: Mpt. (ethanol–acetone) 137–138 °C (Lit. 131–133 °C;8Rf [SiO2, EtOAc–n-hexane (1[thin space (1/6-em)]:[thin space (1/6-em)]3)] = 0.1; [α]22D = 0 (c = 0.5 g/100 mL, MeOH); UV (H2O): λmax = 233.0 nm (A = 0.316, c = 9.9 × 10−4 g/100 mL); IR (ATR-FTIR): 2721.0 (C–H), 2457.0 (NH2+) and 1601.0 cm−1 (C[double bond, length as m-dash]C, aromatic); 1H-NMR (400 MHz, CDCl3) δ1H (ppm) = 9.71 (2H, bs, CH2CH(CH3)NH2+CH3), 7.21 (1H, dd, J = 5.0, 0.92 Hz, thiophene-5H), 7.08 (1H, dd, J = 5.0, 3.5 Hz, thiophene-4H), 6.98 (1H, dd, J = 3.5, 0.92 Hz, thiophene-3H), 3.62 (1H, dd, J = 14.0, 4.1 Hz, CH2CH(CH3)NH2+CH3), 3.34 (1H, ddq, J = 14.0, 10.3, 4.1 Hz, CH2CH(CH3)NH2+CH3), 3.18 (1H, dd, 14.0, 10.3 Hz,
CH2CH(CH3)NH2+CH3), 2.71 (3H, s, CH2CH(CH3)NH2+CH3) and 1.43 ppm (3H, d, J = 6.9 Hz, CH2CH(CH3)NH2+CH3); 13C-NMR (100 MHz, CDCl3) δ13C (ppm) = 137.6 (thiophene-2C), 127.4 (thiophene-3C), 127.2 (thiophene-4C), 125.1 (thiophene-5C), 57.3 (CH2CH(CH3)NH2+CH3), 33.6 (CH2CH(CH3)NH2+CH3), 30.4 (CH2CH(CH3)NH2+CH3) and 15.9 ppm (CH2CH(CH3)NH2+CH3); LRMS (EI-, 70 eV): m/z = 154 (0.5%, [M − H]), 140 (1), 97 (36), and 58 (100); HRMS (ESI+, 15 eV) calculated for [M + H] C8H14NS: 156.0841, found: 156.0844.
An integrated Agilent HP Series 1100 Liquid Chromatograph (Agilent Technologies, Wokingham, UK) with an in-line degasser, 100-place auto-injector, and diode-array UV absorbance detector (monitoring at 233 nm (MPA) and 207 nm (2-AI) was used to perform reverse phase high-performance liquid chromatography. ChemStation for LC (Ver. 10.02) software (Agilent Technologies, Wokingham, UK) was used to analyze the data.
Aqueous acetonitrile was used as the mobile phase:[thin space (1/6-em)]:[thin space (1/6-em) 10 mM ammonium formate buffer (pH 3.5 0.02) (10[thin space (1/6-em)]:[thin space (1/6-em)]90 v/v); flow rate 1.2 mL min1; injection volume 10 L Each calibration standard was injected six times in duplicate. HiChrom Limited provided the stationary phase for the investigation (ACE 3 C18, 150 mm 4.6 mm i.d., particle size: 3 m) (Reading, UK). The column was fitted with a guard cartridge (ACE 3 C18) and maintained at an isothermal temperature of 22 °C with an Agilent HP Series 1100 column oven with a programmed controller (Agilent Technologies, Wokingham, UK) (Agilent Technologies, Wokingham, UK).
