Characterization of 4-Chloromethcathinone

Michael Martin, Donna M. Iula, Ph.D., Cayman Chemical Company, Ann Arbor, MI 48108Address

Lauren McCormick, Kentucky State Police Eastern Laboratory Branch, Ashland, KY

Table of contents:

Part 1: Cayman Chemical Data:

Figure 1. 4-Chloromethcathinone GC/MS Data

Figure 2. 4-Chloromethcathinone FTIR Data

Figure 3. 4-Chloromethcathinone 1H NMR Data

Figure 4. 4-Chloromethcathinone 1H NMR Data, Enlarged

Figure 5. 4-Chloromethcathinone ESI-MS Data

Part 2: Kentucky State Police Eastern Laboratory Branch Data:

Figure 6. 4-Chloromethcathinone EI/MS Data

Figure 7. 4-Chloromethcathinone Expanded EI/MS Data

Figure 8. 4-Chloromethcathinone FTIR Diamond ATR Data

Figure 9. 4-Chloromethcathinone Expanded FTIR/ATR Data

Part 3: References
 Part 1. Cayman Chemical Company Data

Name: 4-Chloromethcathinone
Synonyms: 4-CMC, clephedrone
O CH3

CAS#: N/A NH
Molecular Formula: C10H12ClNO
Molecular Weight: 197.66 g/mol CH3
Cl
SMILES: O=C(c1ccc(Cl)cc1)C(C)NC
InChl Key: UEJBEYOXRNGPEI-UHFFFAOYAF
InChl: InChI=1/C10H12ClNO/c1-7(12-2)10(13)8-3-5-9(11)6-4-8/h3-7,12H,1-2H3

Background:
4-Chloromethcathinone (also referred to as clephedrone or 4-CMC) is one of many designer
synthetic cathinones that has been sold on the illicit drug market.1 4-CMC is a derivative of US
regulated Schedule I controlled substance methcathinone. The only difference between the
two is that 4-CMC has a chlorine in the para position on the phenyl ring. While pharmacological
data for this compound does not exist, it has been published that the bromine analogue (4-
bromomethcathinone or 4-BMC) acts as a serotonin and norepinephedrine reuptake
inhibitor.2,3

1-Forensic Sci Int. 2014, 244, e56-e59.

2-Drug Develop Res. 2003, 60, 252-260
3-Naunyl Schmiedebergs Arch Pharmacol. 2002, 365(4), 457-461.

Page 2 of 15 August 5, 2015

Gas chromatography/Mass spectrometry:
Experiment Parameters: Instrument: Agilent 6890 GC / 5973 MSD

Column: 30mx0.32mm, 0.5um Rtx-5MS

Carrier Gas: Helium Flow: 2mL/min

Inlet temp: 300 oC 15:1 split

Oven Program: Initial temp: 50 oC, Ramp to 300 oC at 30 oC /min,

Hold at 300 oC for 5.67 minutes

Transfer Line Temp: 300 oC

MS Source: 230oC

MS Quad: 150oC

Mass Scan Range: 40-600 amu

Threshold: 150

Tune File: stune.u

Page 3 of 15 August 5, 2015

Figure 1: Gas Chromatography/Mass Spectrometry of 4-Chloromethcathinone

Page 4 of 15 August 5, 2015

Figure 2. Fourier Transform Infrared Spectroscopy of 4-Chloromethcathinone

Experiment Parameters:
Instrument: Perkin Elmer Spectrum 65
Number of scans: 16 (background subtracted)
Resolution: 4 cm-1
Scan Range: 600-4000 cm-1
Sample prepared as KBr pellet

Page 5 of 15 August 5, 2015

Figure 3. 1H Nuclear Magnetic Resonance Spectroscopy of 4-Chloromethcathinone

Page 6 of 15 August 5, 2015

Figure 4. 1H Nuclear Magnetic Resonance Spectroscopy of 4-Chloromethcathinone, Enhanced
for Detail

Page 7 of 15 August 5, 2015

Figure 5. ESI-MS of 4-Chloromethcathinone

Page 8 of 15 August 5, 2015

 Part 2. Kentucky State Police Eastern Laboratory Branch Data

Name: 4-Chloromethcathinone

Synonyms: 1-(4-chlorophenyl)-2-(methylamino)-1- O CH3

propanone; Clephedrone; 4-CMC
CAS#: N/A NH
Molecular Formula: C10H12ClNO
Molecular Weight: 197.66 g/mol CH3
Cl
SMILES: O=C(c1ccc(Cl)cc1)C(C)NC
InChl Key: WJAQVQFSQUVTAY-UHFFFAOYSA-N
InChl: InChI=1/C10H12ClNO/c1-7(12-2)10(13)8-3-5-9(11)6-4-8/h3-7,12H,1-2H3

Page 9 of 15 August 5, 2015

Gas chromatography/Mass spectrometry:
Sample Preparation: Approximately 1mg/mL in Methanol

Instrument: Agilent gas chromatograph operated in split mode with MS detector

GC Parameter: Column: Zebron ZB-DRUG-1 (10m x 0.18mm x 0.18m)

Carrier Gas: Helium

Oven Program:

Temperature Program: 100C initial temperature for 0.5 min, ramp to

280C at 40/min, hold final temperature for 8.5 min

Pressure Program: 5psi initial pressure for 0.5 min, ramp to 15 psi at
75psi/min and hold for 6 min, ramp to 40psi at 150psi/min and hold for
0.5 min

Injection parameter: Injector Volume: 1L

Split ratio: 50:1

MS Parameters: Temperatures:

Injector: 250C

MSD transfer line: 280oC

MS Source: 230oC

MS Quad: 150oC

Mass Scan Range: 40-550amu

Threshold: 150

Tune File: atune.u

Page 10 of 15 August 5, 2015

Figure 6: EI Mass Spectrum of 4-Chloromethcathinone
Abundance

T I C : 4 - c h lo r o m e t h c a t h in o n e s t d m s . D \ d a t a . m s
140000
2.726
130000
120000
110000
100000
90000
80000
70000
60000
50000
40000
30000
20000
10000

1 .0 0 2 .0 0 3 .0 0 4 .0 0 5 .0 0 6 .0 0 7 .0 0 8 .0 0 9 .0 0 1 0 .0 0 1 1 .0 0 1 2 .0 0 1 3 .0 0
T im e - - >

A b u n d a n c e

S c a n 3 5 1 ( 2 . 7 2 6 m in ) : 4 - c h lo r o m e t h c a t h in o n e s t d m s . D \ d a t a . m s
5 8
7 5 0 0 0

7 0 0 0 0

6 5 0 0 0

6 0 0 0 0

5 5 0 0 0

5 0 0 0 0

4 5 0 0 0

4 0 0 0 0

3 5 0 0 0

3 0 0 0 0

2 5 0 0 0

2 0 0 0 0

1 5 0 0 0

1 0 0 0 0
7 5 1 1 1
5 0 0 0 1 3 9
4 2 5 0
8 5 1 0 3 1 2 5 1 4 71 5 4 1 6 6 1 8 2 1 9 5
0
4 0 5 0 6 0 7 0 8 0 9 0 1 0 0 1 1 0 1 2 0 1 3 0 1 4 0 1 5 0 1 6 0 1 7 0 1 8 0 1 9 0 2 0 0
m / z - ->

Page 11 of 15 August 5, 2015

Figure 7: Expanded Mass Spectrum of 4-Chloromethcathinone

A b u n d a n c e

S c a n 3 5 1 ( 2 . 7 2 6 m in ) : 4 - c h lo r o m e t h c a t h in o n e s t d m s . D \ d a t a . m s
5 8
9 5 0 0

9 0 0 0

8 5 0 0 E X P A N D E D

8 0 0 0

7 5 0 0

7 0 0 0

6 5 0 0 7 5 1 1 1

6 0 0 0

5 5 0 0

5 0 0 0

4 5 0 0 1 3 9

4 0 0 0

3 5 0 0

3 0 0 0

2 5 0 0 4 2
5 0
2 0 0 0

1 5 0 0

1 0 0 0
8 5 1 4 7
1 2 5 1 6 6
5 0 0 1 0 3
1 5 4 1 8 2 1 9 5
0
4 0 5 0 6 0 7 0 8 0 9 0 1 0 0 1 1 0 1 2 0 1 3 0 1 4 0 1 5 0 1 6 0 1 7 0 1 8 0 1 9 0 2 0 0
m / z - - >

Page 12 of 15 August 5, 2015

Figure 8. FTIR/ATR Spectrum of 4-Chloromethcathinone

Experiment Parameters:
Instrument: FT-IR with diamond ATR attachment
Number of Scans: 64
Number of Background Scans: 64
Resolution: 4 cm-1

Page 13 of 15 August 5, 2015

Figure 9. Expanded FTIR/ATR Spectrum of 4-Chloromethcathinone

Page 14 of 15 August 5, 2015

Part 3. References:

M. Taschwer, J. A. Wei, O. Kunert, M. G. Schmid. Analysis and characterization of the novel

psychoactive drug 4-chloromethcathinone (clephedrone). Forensic Science International. 244
(2014) e56e59.

Page 15 of 15 August 5, 2015