IP Library Granted Patent US 8,906,633
Granted Patent B2
US 8,906,633 · App. 13/332,042 · Granted Dec 9, 2014

Detection of synthetic cannabinoids

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Quick Facts
Patent No.
US 8,906,633
App. No.
13/332,042
Granted
Dec 9, 2014
Kind
B2
Abstract

The invention describes methods and kits for detecting and determining current and future synthetic cannabinoids from the JWH and CP families. Unique antibodies derived from novel immunogens enable said methods and kits.

Claims (34)

1. An antibody raised to an immunogen of structure (a),

wherein

the crosslinker is —X—Y—, wherein X is linked to the N atom of the indole ring and Y is linked to the accm,

wherein Y is selected from the group consisting of carbonyl, amino, thio and azo, or Y is generated by reacting accm with X which is substituted with a terminal functional group selected from the group consisting of maleimide, isocyanate, isothiocyanate, aldehyde and dithiopyridine, and

wherein X is —(CO) n -D-, wherein D is linked to Y, wherein

n=0 or 1, and

D is a C 1-10 substituted or unsubstituted straight chain alkylene or arylene moiety, and

wherein accm is an antigenicity conferring carrier material,

wherein the antibody has an average cross-reactivity, relative to JWH-018, of less than 0.28% to serotonin, 4-methoxypsilocin, δ-9-THC, cannabinol, 11-hydroxy-δ-9-THC, CP 47,497, 3-carboxy-N-pentyl-1H-indole, 3-carboxy-1H-indole, 3-carboxymethyl-5-hydroxy-1H-indole and 5-hydroxytryptophol; and,

wherein the antibody has an average cross-reactivity, relative to JWH-018, of at least 100% to JWH-073, JWH-200, JWH-018 N-pentanoic acid metabolite (M1), JWH-018 5-hydroxyindole metabolite (M2), JWH-018 N-(5-hydroxypentyl) metabolite (M4), JWH-018 6-hydroxyindole metabolite (M5), and 1-(5-fluoropentyl)indol-3-yl-(1-naphthyl)methanone; and

wherein the antibody has an average cross-reactivity, relative to JWH-018, of less than 6.78% to JWH-398.

2. The antibody of claim 1 , wherein the antibody binds to 3-(1-naphthoyl)-1H-indole.

3. The antibody of claim 1 , wherein Y=carbonyl, n=0 and D=1,5-pentylene.

4. The antibody of claim 1 having an IC 50 of greater than 750 ng/ml for serotonin, 4-methoxypsilocin, δ-9-THC, cannabinol, 11-hydroxy-δ-9-THC, CP 47,497, 3-carboxy-N-pentyl-1H-indole, 3-carboxy-1H-indole, 3-carboxymethyl-5-hydroxy-1H-indole and 5-hydroxytryptophol.

5. A method of detecting or determining synthetic cannabinoids of the JWH family, a metabolite thereof or a combination thereof in an in vitro sample of an individual or in a solution derived from a substance suspected of containing synthetic cannabinoids, the method comprising

contacting the sample or solution with at least one detecting agent and at least one antibody of claim 1 ;

detecting or determining the quantity of the at least one detecting agent; and

deducing from calibrators the presence of or amount of a molecule or molecules of the JWH family, the metabolite thereof or the combination thereof in the sample or solution.

6. The method of claim 5 , wherein the synthetic cannabinoids to be detected or determined are selected from the group consisting of JWH-018, JWH-073 and JWH-200.

7. The method of claim 5 , wherein the crosslinker is —X—Y— wherein Y is carbonyl and X is 1,5-pentylene.

8. A kit for detecting or determining at least one molecule of the JWH family, a metabolite thereof or a combination thereof, the kit comprising at least one antibody raised to the immunogen of structure (a):

wherein:

the crosslinker is —X—Y—, wherein X is linked to the N atom of the indole ring and Y is linked to the accm,

wherein Y is selected from the group consisting of carbonyl, amino, thio and azo, or Y is generated by reacting accm with X which is substituted with a terminal functional group selected from the group consisting of maleimide, isocyanate, isothiocyanate, aldehyde and dithiopyridine, and

wherein X is —(CO) n -D-, wherein D is linked to Y, wherein

n=0 or 1, and

D is a C 1-10 substituted or unsubstituted straight chain alkylene or arylene moiety, and

wherein accm is an antigenicity conferring carrier material,

wherein the antibody has an average cross-reactivity, relative to JWH-018, of less than 0.28% to serotonin, 4-methoxypsilocin, δ-9-THC, cannabinol, 11-hydroxy-δ-9-THC, CP 47,497, 3-carboxy-N-pentyl-1H-indole, 3-carboxy-1H-indole, 3-carboxymethyl-5-hydroxy-1H-indole and 5-hydroxytryptophol;

wherein the antibody has an average cross-reactivity, relative to JWH-018, of at least 100% to JWH-073, JWH-200, JWH-018 N-pentanoic acid metabolite (M1), JWH-018 5-hydroxyindole metabolite (M2), JWH-018 N-(5-hydroxypentyl) metabolite (M4), JWH-018 6-hydroxyindole metabolite (M5), and 1-(5-fluoropentyl)indol-3-yl-(1-naphthyl)methanone; and

wherein the antibody has an average cross-reactivity, relative to JWH-018, of less than 6.78% to JWH-398.

9. The kit of claim 8 , wherein Y=carbonyl, n=0 and D=1,5-pentylene.

10. The kit of claim 8 , wherein the antibody has an IC 50 of greater than 750 ng/ml for serotonin, 4-methoxypsilocin, δ-9-THC, cannabinol, 11-hydroxy-δ-9-THC, CP 47,497, 3-carboxy-N-pentyl-1H-indole, 3-carboxy-1H-indole, 3-carboxymethyl-5-hydroxy-1H-indole and 5-hydroxytryptophol.

11. The kit of claim 8 , wherein the antibody binds to 3-(1-naphthoyl)-1H-indole.

Assignments (3)
CORRECTIVE ASSIGNMENT TO CORRECT THE NATURE OF CONVENYANCE PREVIOUSLY RECORDED AT REEL: 055950 FRAME: 0471. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Apr 20, 2021
From: RANDOX LABORATORIES LIMITED
To: NORTHERN BANK LIMITED
Reel/Frame 056210/0055 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 15, 2021
From: RANDOX LABORATORIES LIMITED
To: NORTHERN BANK LIMITED
Reel/Frame 055950/0471 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 12, 2012
From: BENCHIKH, ELOUARD; FITZGERALD, STEPHEN PETER; INNOCENZI, PAUL JOHN; LOWRY, PHILIP ANDREW; MCCONNELL, IVAN ROBERT
To: RANDOX LABORATORIES LIMITED
Reel/Frame 027846/0964 →