Methoxy Morphinan; HQ 956444; Revocation of HQ 958619

HQ 962209 May 6, 1999 CLA-2 RR:CR:GC 962209 MGM CATEGORY: Classification TARIFF NO.: 2933.40.26 Mr. Kevin Maher C-Air Custom House Brokers-Forwarders, Inc. 153-66 Rockaway Boulevard Jamaica, New York 11434 RE: Methoxy Morphinan; HQ 956444; Revocation of HQ 958619 Mr. Maher: This is in reference to the classification of methoxy morphinan under the Harmonized Tariff Schedule of the United States (HTSUS). New York Ruling Letter (NY) 889472, which was issued to you on behalf of Reddy-Cheminor Inc. on September 23, 1993, classified methoxy morphinan in subheading 2933.90.80, HTSUS. This provision has since been renumbered subheading 2933.90.79, HTSUS. Headquarters Ruling Letter (HQ) 958619, issued to you on April 15, 1998, revoked NY 889472 and classified methoxy morphinan in subheading 2933.40.70, HTSUS. We have reconsidered HQ 958619 and find it to be in error. FACTS: Methoxy morphinan (C17H23NO;CAS Nos. 124431-47-6 and 1531-25-5) is a polycyclic compound used in the synthesis of dextromethorphan hydrobromide, a cough suppressant. It consists of four ring structures: piperidine ortho-fused to hexane and bridged by another ring structure which is fused to methoxybenzene (anisole). Methoxy morphinan must undergo two reaction steps to form dextromethorphan hydrobromide. It is first treated with methanal (formaldehyde), methanoic acid (formic acid), and sodium hydroxide to form dextromethorphan (C18H25NO;CAS No. 125-71-3). Dextromethorphan differs from methoxy morphinan in that it has a methyl group bound to nitrogen rather than a hydrogen. Dextromethorphan is treated with hydrombromic acid to form dextromethorphan hydrobromide (C18H26NO.Br). The entire ring structure of methoxy morphinan remains intact throughout these reaction steps.  ISSUE: Whether methoxy morphinan is a “drug” under the HTSUS? LAW AND ANALYSIS: Merchandise imported into the United States is classified under the HTSUS. Tariff classification is governed by the principles set forth in the General Rules of Interpretation (GRIs) and, in the absence of special language or context which requires otherwise, by the Additional U.S. Rules of Interpretation. The GRIs and the Additional U.S. Rules of Interpretation are part of the HTSUS and are to be considered statutory provisions of law for all purposes. GRI 1 requires that classification be determined first according to the terms of the headings of the tariff schedule and any relative section or chapter notes and, unless otherwise required, according to the remaining GRIs taken in their appropriate order. GRI 6 requires that the classification of goods in the subheadings of headings shall be determined according to the terms of those subheadings, any related subheading notes and mutatis mutandis, to the GRIs. In understanding the language of the HTSUS, the Explanatory Notes (ENs) of the Harmonized Commodity Description and Coding System may be utilized. The ENs, although not dispositive or legally binding, provide a commentary on the scope of each heading, and are generally indicative of the proper interpretation of the HTSUS. See, T.D. 89-80, 54 Fed. Reg. 35127 (August 23, 1989). The following portion of heading 2933, HTSUS, is relevant to the classification of this merchandise: 2933 Heterocyclic compounds with nitrogen hetero-atom(s) only: 2933.40 Compounds containing a quinoline or isoquinoline ring-system (whether or not hydrogenated), not further fused: Other: Drugs: 2933.40.26 Other 2933.40.30 Pesticides Other: 2933.40.60 Products described in additional U.S. note 3 to section VI A heterocyclic compound is an organic compound “composed of one or more rings, and which contain in the ring(s), in addition to the carbon atoms, atoms of other elements.” General EN, Subchapter X, Chapter 29, HTSUS. Methoxy morphinan meets this description, thus it is a heterocyclic compound; as nitrogen is the only element other than carbon found in the ring structure of methoxy morphinan, it is a “heterocyclic compound[] with nitrogen hetero-atom(s) only,” properly classified in heading 2933, HTSUS. Subheading 2933.40 is limited to compounds containing a quinoline or isoquinoline ring-system. Quinoline and isoquinoline are made up of a six-membered ring of carbon fused to a six-membered ring containing five carbons and one nitrogen. They differ only in the position of the nitrogen relative to the six-membered carbon ring. In chemistry, these terms refer to compounds having the chemical formula C9H7N, and consisting of a benzene ring fused to a pyridine ring (where each atom of each ring is sp2 hybridized). However, the tariff language “whether or not hydrogenated” evinces an intent to include compounds with the appropriate ring structure, whether the ring’s atoms are single or double bonded to one another. See HQ 956444, dated October 24, 1995; EN 29.33 (D)(8), (9) (where compounds containing ring structures which do not meet the strict definition of quinoline or isoquinoline are included in subheading 2933.40). Subheading 2933.40, HTSUS, excludes compounds where the quinoline or isoquinoline ring-system is “further fused.” Rings are fused where they have one, and only one, common bond and have two, and only two, common atoms. General ENs, Chapter 29 (IJ). The isoquinoline moiety of methoxy morphinan shares two bonds with a ring structure which in turn shares one bond with the methoxybenzene ring; thus isoquinoline is bridged by this ring structure but not fused to it. See HQ 956444; EN 29.33 (D)(8), (9) (where compounds containing the same ring structures as methoxy morphinan are included in subheading 2933.40). Within subheading 2933.40, HTSUS, are several eo nomine provisions and a residual, or “other,” provision. As methoxy morphinan is not described by any of the more descriptive provisions, it falls within the residual provision. This residual provision provides for “drugs,” “pesticides,” and “other.” Under the Tariff Schedules of the United States (TSUS), predecessor to the HTSUS, the term “drugs” was defined as “those substances having therapeutic or medicinal properties and chiefly used as medicines or as ingredients in medicines.” TSUS Schedule 4, part 1, subpart C, headnote 9. In Austin Chemical Co., Inc. v. U.S., the court addressed the issue of whether mandelic acid is a drug under the TSUS. Austin Chemical Co. v. U.S., 11 CIT 130, 659 F.Supp 229 (CIT 1987), aff’d, Austin Chemical Co., Inc. v. U.S., 835 F.2d 1423, 6 Fed. Cir. (T) (Fed. Cir. 1987). Mandelic acid is one of several compounds from which a beta-lactam antibiotic is synthesized. Synthesis of the antibiotic is a multi-step process during which the mandelic acid undergoes various chemical changes. When the synthesis is complete, the antibiotic has a mandelic acid moiety, or major portion, of the original mandelic acid molecule. This mandelic acid moiety protects the beta-lactam portion of the drug from destructive bacterial enzymes, thereby enhancing the drug’s effectiveness. Austin 835 F.2d at 1424. The court held that therapeutic properties include the imparting of properties to the other substances which are necessary to produce an effective drug. Austin 835 F.2d at 1426. Because mandelic acid imparts important properties to the drug, the court found that it had “therapeutic properties.” The court then turned to the question of whether or not mandelic acid was used as an “ingredient in medicines.” The trial court had held that “before the chemical reaction occurs, the component substances of the compound are properly deemed ingredients.” Austin 11 CIT at 135. That is, the components from which the ultimate product is synthesized are ingredients in medicines. The CAFC stated of this holding, “The court did not err in holding that D(-) mandelic acid was used as an ingredient in medicine within the TSUS definition of drug.” Austin 835 F.2d at 1426. Thus mandelic acid was found to have therapeutic properties and to be used as an ingredient in medicine, and was therefore properly classified as a “drug” under the TSUS. This definition of the term “drugs” was held to continue extant as the common and commercial meaning of the term under the HTSUS. Lonza, Inc. v. U.S., 18 CIT 230, 849 F.Supp 51 (CIT 1994), aff’d, Lonza, Inc. v. U.S., 46 F.3d 1098 (Fed. Cir. 1995) (wherein the Court of Appeals adopted the opinion of the CIT which was attached, in its entirety, to the CAFC opinion as an appendix). In Lonza, the classification of ADC-6, an acyclic organic compound, was at issue. The court stated “ADC-6 is properly characterized as having therapeutic properties because the elements it imparts are crucial to the ultimate formation of an effective antibiotic. This is the standard sanctioned by our appellate court.” Lonza 18 CIT at 237 (citing Austin 835 F.2d at 1426). The court goes on to state “the TSUS definition of ‘drugs’ survives as the common and commercial meaning of the term under the HTS.” Lonza 18 CIT at 239. Thus in determining whether merchandise is a drug, we use the following definition: “those substances having therapeutic or medicinal properties and chiefly used as medicines or as ingredients in medicines.” Methoxy morphinan contributes the entire ring structure to dextromethorphan hydrobromide, the ultimate product administered to humans as a medicine. The two compounds differ only in that dextromethorphan hydrobromide has a methyl group attached to the nitrogen and it has undergone acidification. Thus, we can infer that methoxy morphinan contributes elements crucial to the antitussive function of dextromethorphan hydrobromide. This is corroborated by the similarity of the ring structure of methoxy morphinan to that of the antitussives found in Patent Numbers 5,714,483, issued February 3, 1998, and 5,739,145, issued April 14, 1998. Methoxy morphinan therefore has “therapeutic properties.” It is a component substance which reacts to form the ultimate product, thus it is an “ingredient in medicine.” Austin 11 CIT at 135. As a substance having therapeutic properties, used as an ingredient in medicine, methoxy morphinan is a “drug” within the meaning of that term in the HTSUS. HOLDING: Methoxy morphinan is classified in subheading 2933.40.26, HTSUS, as an “other” drug containing an isoquinoline ring system, not further fused. Sincerely, John Durant, Director Commercial Rulings Division