US4438207A
Expired / Lapsed
US
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Radioimmunoassay for cannabinoids
Assignee: Hoffmann La Roche Inc
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Filing: 1981-04-13
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Granted: 1984-03-20
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Expires: 2001-04-13
Abstract
Abstract An improved immunoassay for detecting cannabinoids is described. This immunoassay is characterized by utilizing, as reagents, antibody, 125 I-radiolabeled antigen, an unlabeled antigen and an anion exchange resin for separation of labeled and unlabeled antigen. The iodinated tetrahydrocannabinol moiety is stabilized by the addition of small quantities of antioxidants such as butylated hydroxy toluene.
Inventors
- 👤 Kenneth E. Fahrenholtz
- 👤 John E. Heveran
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 01:40
CPC Classifications
G; G01; G01N; G01N33/00; G01N33/48; G01N33/50; G01N33/94; G01N33/948; C; C07; C07D; C07D311/00; C07D311/02; C07D311/78; C07D311/80; Y; Y10; Y10S; Y10S436/00; Y10S436/804; Y10S436/807; Y10S436/808; Y10S436/815
Claims Analysis
Total Claims: 24
Claim 1
Independent Claim
1 words
(6aR,10aR)-4-[(6a,7,10,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-yl)oxy]-N-[2-(4-hydroxyphenyl)ethyl]-butanamide.
Claim 2
Dependent Claim
1 words
(6aR,10aR)-4-[(6a,7,10,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-yl)oxy]-N-[2-(4-hydroxyphenyl)ethyl]-butanamide.
Claim 3
Dependent Claim
2 words
125 I-(6aR,10aR)-4-[(6a,7,10,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-yl)oxy]-N-[2-(4-hydroxyphenyl)ethyl]-butanamide.
Claim 4
Dependent Claim
2 words
125 I-(6aR,10aR)-4-[(6a,7,10,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-yl)oxy]-N-[2-(4-hydroxyphenyl)ethyl]-butanamide.
Claim 5
Dependent Claim
1 words
(6aR,10aR)-4-[(6a,7,8,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-yl)oxy]-N-[2-(4-hydroxyphenyl)ethyl]-butanamide.
Claim 6
Dependent Claim
1 words
(6aR,10aR)-4-[(6a,7,8,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-yl)oxy]-N-[2-(4-hydroxyphenyl)ethyl]-butanamide.
Claim 7
Dependent Claim
2 words
125 I-(6aR,10aR)-4-[(6a,7,8,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-yl)oxy]-N-[2-(4-hydroxyphenyl)ethyl]-butanamide.
Claim 8
Dependent Claim
2 words
125 I-(6aR,10aR)-4-[(6a,7,8,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-yl)oxy]-N-[2-(4-hydroxyphenyl)ethyl]-butanamide.
Claim 9
Dependent Claim
9 words
An immunogen comprising bovine serum albumen and (6aR,10aR)-4-[(6a,7,10,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-yl)oxy]butanoic acid.
Claim 10
Dependent Claim
9 words
An immunogen comprising bovine serum albumen and (6aR,10aR)-4-[(6a,7,10,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-yl)oxy]butanoic acid.
Claim 11
Dependent Claim
14 words
An immunogenic compound derived from the reaction of (6aR,10aR)-4-(6a,7,8,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-yl)oxy]butanoic acid and bovine serum albumen.
Claim 12
Dependent Claim
14 words
An immunogenic compound derived from the reaction of (6aR,10aR)-4-(6a,7,8,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-yl)oxy]butanoic acid and bovine serum albumen.
Claim 13
Independent Claim
42 words
A method for the production of antibody useful for the assay of tetrahydrocannabinol, which comprises eliciting said antibody in the blood of a host animal by immunization with an immunogenic compound derived from the reaction of (6aR,10aR)-4-(6a,7,8,10a-tetrahydro-6,69-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-yl)oxy]butanoic acid and bovine serum albumen.
Claim 14
Independent Claim
42 words
A method for the production of antibody useful for the assay of tetrahydrocannabinol, which comprises eliciting said antibody in the blood of a host animal by immunization with an immunogenic compound derived from the reaction of (6aR,10aR)-4-(6a,7,8,10a-tetrahydro-6,69-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-yl)oxy]butanoic acid and bovine serum albumen.
Claim 15
Independent Claim
120 words
A method for the assay of tetrahydrocannabinol in a sample which method comprises mixing said sample with fixed amounts of an 125 I-labeled tetrahydrocannabinol derivative selected from the group comprising 125 I-(6aR,10aR)-4-[(6a,7,10,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]-pyran-1-yl)oxy]-N-[2-(4-hydroxyphenyl)ethyl]-butanamide and 125 I-(6aR,10aR)-4-[(6a,7,8,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]-pyran-1-yl)oxy]-N-[2-(4-hydroxyphenyl)ethyl]-butanamide and an antibody which will selectively complex with tetrahydrocannabinol, said antibody being elicited in the blood of a host animal by immunization with an immunogenic compound derived from the reaction of [(6aR,10aR)-4-(6a,7,8,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-yl)oxy]butanoic acid and bovine serum albumen, separating antibody bound tetrahydrocannabinol and 125 I-labeled derivative (collectively called "antigen") from free antigen by means of an anion exchange resin and, then, measuring the radioactivity of either the free or bound antigen and comparing said value to values obtained previously with samples containing known amounts of tetrahydrocannabinol.
Claim 16
Independent Claim
120 words
A method for the assay of tetrahydrocannabinol in a sample which method comprises mixing said sample with fixed amounts of an 125 I-labeled tetrahydrocannabinol derivative selected from the group comprising 125 I-(6aR,10aR)-4-[(6a,7,10,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]-pyran-1-yl)oxy]-N-[2-(4-hydroxyphenyl)ethyl]-butanamide and 125 I-(6aR,10aR)-4-[(6a,7,8,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]-pyran-1-yl)oxy]-N-[2-(4-hydroxyphenyl)ethyl]-butanamide and an antibody which will selectively complex with tetrahydrocannabinol, said antibody being elicited in the blood of a host animal by immunization with an immunogenic compound derived from the reaction of [(6aR,10aR)-4-(6a,7,8,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-yl)oxy]butanoic acid and bovine serum albumen, separating antibody bound tetrahydrocannabinol and 125 I-labeled derivative (collectively called "antigen") from free antigen by means of an anion exchange resin and, then, measuring the radioactivity of either the free or bound antigen and comparing said value to values obtained previously with samples containing known amounts of tetrahydrocannabinol.
Claim 17
Dependent Claim
118 words
A test kit for the detection or assay of tetrahydrocannabinol in a sample comprising: a. a first container means containing a preselected amount of an 125 I-labeled tetrahydrocannabinol derivative selected from the group comprising 125 I-(6aR,10aR)-4-[6a,7,10,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-yl)oxy]-N-[2-(4-hydroxyphenyl)ethyl]butanamide and 125 I-(6aR,10aR)-4-[(6a,7,8,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-yl)oxy]-N-[2-(4-hydroxyphenyl)ethyl]butanamide; b. a second container means containing a preselected amount of an antibody reagent which will selectively complex with both tetrahydrocannabinol and said 125 I-labeled derivative (collectively called "antigen") said antibody being elicited in the blood of a host animal by immunization with an immunogenic compound derived from the reaction of [(6aR,10aR)-4-(6a,7,8,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-yl)oxy]butanoic acid and bovine serum albumen; and, c. a third container means containing a preselected amount of an anion exchange resin for separating antibody bound antigen from free antigen.
Claim 18
Dependent Claim
118 words
A test kit for the detection or assay of tetrahydrocannabinol in a sample comprising: a. a first container means containing a preselected amount of an 125 I-labeled tetrahydrocannabinol derivative selected from the group comprising 125 I-(6aR,10aR)-4-[6a,7,10,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-yl)oxy]-N-[2-(4-hydroxyphenyl)ethyl]butanamide and 125 I-(6aR,10aR)-4-[(6a,7,8,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-yl)oxy]-N-[2-(4-hydroxyphenyl)ethyl]butanamide; b. a second container means containing a preselected amount of an antibody reagent which will selectively complex with both tetrahydrocannabinol and said 125 I-labeled derivative (collectively called "antigen") said antibody being elicited in the blood of a host animal by immunization with an immunogenic compound derived from the reaction of [(6aR,10aR)-4-(6a,7,8,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-yl)oxy]butanoic acid and bovine serum albumen; and, c. a third container means containing a preselected amount of an anion exchange resin for separating antibody bound antigen from free antigen.
Claim 19
Dependent Claim
37 words
The test kit of claim 9, further comprising a fourth container means containing a preselected amount of a positive urine control which contains a known concentration of tetrahydrocannabinol, against which samples to be assayed can be compared.
Claim 20
Dependent Claim
33 words
The test kit of claim 10 further comprising a fifth container means containing a preselected amount of a normal urine control which is free of any tetrahydrocannabinol, for diluting said positive urine control.
Claim 21
Dependent Claim
47 words
The test kit of claim 9 wherein said 125 I-tetrahydrocannabinol derivative reagent comprises a composition containing 500 ml of 125 I-tetrahydrocannabinol derivative possessing radioactivity of 125 microcuries in 0.01 M phosphate buffered saline containing 25% ethanol with 0.1% sodium azide and 0.003 to 0.007% butylated hydroxy toluene.
Claim 22
Dependent Claim
39 words
The test kit of claim 9 wherein said antibody reagent comprises a composition containing 500 ml of tetrahydrocannabinol rabbit antibody diluted in 0.01 M phosphate buffered saline with 0.1% sodium azide, 0.2% bovine gamma globulin and 0.1% Triton X-405.
Claim 23
Dependent Claim
23 words
The test kit of claim 9 wherein the anion exchange resin comprises 1250 ml of AG1 resin suspended in 0.1 M Tris buffer.
Claim 24
Dependent Claim
32 words
The test kit of claim 10 wherein said sample containing known amounts of tetrahydrocannabinol comprises a composition containing 200 ng of tetrahydrocannabinol in 100 ml normal human urine and 0.1% sodium azide.
References Cited (Backward Citations)
GB651653A
Cited
US3656906A
Cited
US3728360A
Cited
US4205952A
Cited
US4207307A
Cited
US4235864A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1987-03-20 | 1987-09-19 | 1988-03-20 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-03-20 | 1991-09-19 | 1992-03-20 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-03-20 | 1995-09-19 | 1996-03-20 | $7700.00 | Window Closed / Lapsed |